NPASS Compound

Structure

CID205727 OpenBabel06191715592D 30 33 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 16 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 13 2 0 0 0 0 9 22 1 0 0 0 0 10 19 1 0 0 0 0 12 17 2 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 26 1 0 0 0 0 14 20 2 0 0 0 0 14 27 1 0 0 0 0 15 9 1 6 0 0 0 15 18 1 0 0 0 0 15 28 1 0 0 0 0 16 23 2 0 0 0 0 16 29 1 0 0 0 0 17 24 1 0 0 0 0 18 11 1 1 0 0 0 18 30 1 0 0 0 0 19 21 2 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.11
Volume:	395.567
LogP:	1.46
LogD:	1.658
LogS:	-4.139
# Rotatable Bonds:	5
TPSA:	116.82
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.605
Synthetic Accessibility Score:	3.511
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.117
MDCK Permeability:	2.546914947743062e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.702
Plasma Protein Binding (PPB):	71.78217315673828%
Volume Distribution (VD):	0.858
Pgp-substrate:	27.718708038330078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.572
CYP2C9-inhibitor:	0.288
CYP2C9-substrate:	0.693
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.589
CYP3A4-inhibitor:	0.556
CYP3A4-substrate:	0.832

ADMET: Excretion

Clearance (CL):	5.168
Half-life (T1/2):	0.768

ADMET: Toxicity

hERG Blockers:	0.318
Human Hepatotoxicity (H-HT):	0.6
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.393
Maximum Recommended Daily Dose:	0.223
Skin Sensitization:	0.574
Carcinogencity:	0.306
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.023

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC205727

Natural Product ID:	NPC205727
*Common Name:**	Cleomiscosin C
IUPAC Name:	(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
Synonyms:	Cleomiscosin C
Standard InCHIKey:	GZXPCBAETDEQAX-CRAIPNDOSA-N
Standard InCHI:	InChI=1S/C21H20O9/c1-25-12-7-11(8-13(26-2)17(12)24)18-15(9-22)28-21-19-10(4-5-16(23)29-19)6-14(27-3)20(21)30-18/h4-8,15,18,22,24H,9H2,1-3H3/t15-,18-/m1/s1
SMILES:	OC[C@H]1Oc2c(O[C@@H]1c1cc(OC)c(c(c1)OC)O)c(OC)cc1c2oc(=O)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465491
PubChem CID:	11464176
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0002545] Coumarinolignans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10346965]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	root	n.a.	PMID[10617409]
NPO1033	Plectranthus nummularius	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11558608]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575966]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	Japan	n.a.	PMID[12542351]
NPO18398	Rhododendron collettianum	Species	Ericaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15577244]
NPO11507	Entada africana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989528]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21550801]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO8872	Streptomyces rishiriensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24079980]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26081757]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[27169184]
NPO10662	Scrippsiella trochoidea	Species	Peridiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8021655]
NPO8872	Streptomyces rishiriensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8931735]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18398	Rhododendron collettianum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15167	Eichhornia crassipes	Species	Pontederiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29756	Aquilaria agallocha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13983	Acer maximowiczianum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7043	Fuligo candida	Species	Physaraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15167	Eichhornia crassipes	Species	Pontederiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6295	Astragalus trojanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11281	Euphorbia fortissima	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18398	Rhododendron collettianum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2787	Cussonia racemosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1033	Plectranthus nummularius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15954	Pyrenula japonica	Species	Pyrenulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29756	Aquilaria agallocha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16326	Scopolia parviflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18071	Euryops pedunculatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16210	Androcymbium palaestinum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16092	Calocephalus knappii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12994	Choriaster granulatus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17917	Thamnophis sirtalis	Species	Colubridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17141	Lonchocarpus longistylus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14865	Vitex limonifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5016	Glossogyne tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11755	Banisteriopsis caapi	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10662	Scrippsiella trochoidea	Species	Peridiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16355	Phyllanthus acutifolius	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14345	Androsace septentrionalis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16900	Aesculus turbinata	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15594	Aplidiopsis confluata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21758	Thiocystis gelatinosa	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1033	Plectranthus nummularius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11507	Entada africana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO742	Aloe saponaria	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15167	Eichhornia crassipes	Species	Pontederiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15954	Pyrenula japonica	Species	Pyrenulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17625	Colchicum hierosolymitanum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13383	Schumanniophyton magnificum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12630	Senecio oxyodontus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14049	Fumaria indica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16326	Scopolia parviflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9786	Monomeria barbata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9358	Pseuduvaria indochinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15740	Garcinia purpurea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18398	Rhododendron collettianum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14507.1	Quercus ithaburensis subsp. macrolepis	Subspecies	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7043	Fuligo candida	Species	Physaraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8872	Streptomyces rishiriensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29062	Hibiscus syriacus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16049	Cryptocarya pleurosperma	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8401	Pteris setuloso-costulata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11684	Iberis sempervirens	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17757	Plectranthus saccatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10751	Bothriocline laxa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11153	Entada polystachya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17600	Gnathotrichus sulcatus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6295	Astragalus trojanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6370	Roemeria carica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17444	Gleichenia japonica	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11281	Euphorbia fortissima	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12341	Axinyssa pitys	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4360	Hendersonula toruloidea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11280	Aphanoascus terreus	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2787	Cussonia racemosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13842	Nepeta caesarea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1219	Theobroma speciosum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14001	Ceroplastes pseudoceriferus	Species	Coccidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO619	Ankistrodesmus braunii	Species	Selenastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13983	Acer maximowiczianum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15449	Echium rubrum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	0.7	ug.mL-1	PMID[510603]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC205727 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	1818
0.2-0.3	4832
0.3-0.4	9844
0.4-0.5	7872
0.5-0.6	4004
0.6-0.7	5307
0.7-0.8	4984
0.8-0.85	1872
0.85-0.9	1465
0.9-0.95	270
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC294522
1.0	High Similarity	NPC120426
1.0	High Similarity	NPC21184
0.993	High Similarity	NPC30688
0.993	High Similarity	NPC176903
0.9859	High Similarity	NPC476348
0.9859	High Similarity	NPC187398
0.9789	High Similarity	NPC15577
0.9789	High Similarity	NPC476347
0.9724	High Similarity	NPC264875
0.9724	High Similarity	NPC120774
0.9724	High Similarity	NPC163598
0.9392	High Similarity	NPC150442
0.9388	High Similarity	NPC213197
0.9371	High Similarity	NPC91492
0.9371	High Similarity	NPC34245
0.9371	High Similarity	NPC7439
0.9371	High Similarity	NPC110067
0.9371	High Similarity	NPC256555
0.9329	High Similarity	NPC8712
0.9324	High Similarity	NPC176186
0.9324	High Similarity	NPC53587
0.9324	High Similarity	NPC169404
0.931	High Similarity	NPC268515
0.931	High Similarity	NPC40222
0.9252	High Similarity	NPC212670
0.9252	High Similarity	NPC206264
0.9252	High Similarity	NPC313334
0.9247	High Similarity	NPC231149
0.9231	High Similarity	NPC300611
0.9225	High Similarity	NPC43500
0.9225	High Similarity	NPC13067
0.9225	High Similarity	NPC164148
0.9195	High Similarity	NPC215060
0.9195	High Similarity	NPC476352
0.9189	High Similarity	NPC114740
0.9184	High Similarity	NPC93924
0.9184	High Similarity	NPC96294
0.9184	High Similarity	NPC48366
0.9184	High Similarity	NPC478237
0.9184	High Similarity	NPC139839
0.9178	High Similarity	NPC205361
0.9167	High Similarity	NPC278469
0.9167	High Similarity	NPC193722
0.9155	High Similarity	NPC126206
0.9155	High Similarity	NPC139548
0.9155	High Similarity	NPC52086
0.9155	High Similarity	NPC95162
0.9155	High Similarity	NPC76336
0.9155	High Similarity	NPC148835
0.9155	High Similarity	NPC20511
0.9122	High Similarity	NPC475250
0.9122	High Similarity	NPC106138
0.9116	High Similarity	NPC41844
0.9116	High Similarity	NPC178129
0.9103	High Similarity	NPC138212
0.9097	High Similarity	NPC83375
0.9097	High Similarity	NPC224876
0.9085	High Similarity	NPC471665
0.9085	High Similarity	NPC471664
0.9085	High Similarity	NPC126682
0.9085	High Similarity	NPC82271
0.9079	High Similarity	NPC284810
0.9048	High Similarity	NPC199928
0.9041	High Similarity	NPC185127
0.9041	High Similarity	NPC471763
0.9038	High Similarity	NPC142614
0.9028	High Similarity	NPC267291
0.9021	High Similarity	NPC38874
0.9021	High Similarity	NPC103976
0.9021	High Similarity	NPC102904
0.9021	High Similarity	NPC176051
0.9021	High Similarity	NPC474886
0.9021	High Similarity	NPC107551
0.9021	High Similarity	NPC326797
0.9021	High Similarity	NPC474282
0.9014	High Similarity	NPC472337
0.8986	High Similarity	NPC52740
0.8966	High Similarity	NPC471389
0.8951	High Similarity	NPC472336
0.8951	High Similarity	NPC471719
0.8951	High Similarity	NPC286843
0.8951	High Similarity	NPC306441
0.8951	High Similarity	NPC16435
0.8951	High Similarity	NPC472334
0.8947	High Similarity	NPC268484
0.8944	High Similarity	NPC135127
0.8944	High Similarity	NPC309953
0.8944	High Similarity	NPC170694
0.8944	High Similarity	NPC310854
0.8944	High Similarity	NPC92830
0.8944	High Similarity	NPC474600
0.8944	High Similarity	NPC111635
0.8912	High Similarity	NPC292443
0.8912	High Similarity	NPC232228
0.8904	High Similarity	NPC469564
0.8889	High Similarity	NPC276490
0.8889	High Similarity	NPC211549
0.8889	High Similarity	NPC142479
0.8889	High Similarity	NPC155015
0.8882	High Similarity	NPC223720
0.8882	High Similarity	NPC149735
0.8881	High Similarity	NPC474206
0.8881	High Similarity	NPC224941
0.8881	High Similarity	NPC234865
0.8881	High Similarity	NPC121812
0.8881	High Similarity	NPC112939
0.8881	High Similarity	NPC470356
0.8881	High Similarity	NPC94750
0.8881	High Similarity	NPC234333
0.8881	High Similarity	NPC311430
0.8881	High Similarity	NPC61946
0.8881	High Similarity	NPC112246
0.8881	High Similarity	NPC260898
0.8881	High Similarity	NPC47398
0.8873	High Similarity	NPC229442
0.8873	High Similarity	NPC36437
0.8873	High Similarity	NPC241341
0.8873	High Similarity	NPC233018
0.8873	High Similarity	NPC277021
0.8873	High Similarity	NPC168059
0.8873	High Similarity	NPC26673
0.8859	High Similarity	NPC97937
0.8859	High Similarity	NPC275125
0.8859	High Similarity	NPC227902
0.8859	High Similarity	NPC170239
0.8851	High Similarity	NPC473909
0.8851	High Similarity	NPC143120
0.8851	High Similarity	NPC274960
0.8851	High Similarity	NPC226722
0.8844	High Similarity	NPC236419
0.8844	High Similarity	NPC478239
0.8844	High Similarity	NPC230157
0.8844	High Similarity	NPC6568
0.8844	High Similarity	NPC252169
0.8836	High Similarity	NPC472520
0.8836	High Similarity	NPC279851
0.8828	High Similarity	NPC245207
0.8828	High Similarity	NPC127218
0.8828	High Similarity	NPC25966
0.8828	High Similarity	NPC319647
0.8828	High Similarity	NPC471388
0.8824	High Similarity	NPC7178
0.8824	High Similarity	NPC62903
0.8819	High Similarity	NPC227503
0.8819	High Similarity	NPC302701
0.8819	High Similarity	NPC474639
0.8819	High Similarity	NPC230734
0.8819	High Similarity	NPC269091
0.8811	High Similarity	NPC309744
0.8811	High Similarity	NPC106215
0.8803	High Similarity	NPC5423
0.8803	High Similarity	NPC35932
0.8803	High Similarity	NPC7903
0.8803	High Similarity	NPC160991
0.8803	High Similarity	NPC137669
0.8803	High Similarity	NPC137949
0.8803	High Similarity	NPC184447
0.8803	High Similarity	NPC16208
0.8803	High Similarity	NPC319969
0.8803	High Similarity	NPC245120
0.88	High Similarity	NPC175976
0.8792	High Similarity	NPC125755
0.8784	High Similarity	NPC471824
0.8782	High Similarity	NPC53889
0.8782	High Similarity	NPC24164
0.8776	High Similarity	NPC140502
0.8776	High Similarity	NPC157816
0.8776	High Similarity	NPC107161
0.8776	High Similarity	NPC145319
0.8776	High Similarity	NPC475084
0.8774	High Similarity	NPC125495
0.8758	High Similarity	NPC476154
0.8758	High Similarity	NPC474656
0.875	High Similarity	NPC214729
0.875	High Similarity	NPC151224
0.875	High Similarity	NPC195022
0.875	High Similarity	NPC164787
0.8742	High Similarity	NPC471823
0.8742	High Similarity	NPC113790
0.8741	High Similarity	NPC11060
0.8741	High Similarity	NPC475840
0.8741	High Similarity	NPC474810
0.8741	High Similarity	NPC263064
0.8733	High Similarity	NPC16269
0.8733	High Similarity	NPC21776
0.8732	High Similarity	NPC472597
0.8732	High Similarity	NPC73738
0.8725	High Similarity	NPC476382
0.8725	High Similarity	NPC163898
0.8725	High Similarity	NPC34927
0.8725	High Similarity	NPC469701
0.8725	High Similarity	NPC476450
0.8725	High Similarity	NPC125617
0.8725	High Similarity	NPC252292
0.8725	High Similarity	NPC34587
0.8725	High Similarity	NPC100998
0.8725	High Similarity	NPC277867
0.8725	High Similarity	NPC161700
0.8725	High Similarity	NPC475096

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC205727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	972
0.2-0.3	2059
0.3-0.4	2589
0.4-0.5	1741
0.5-0.6	916
0.6-0.7	337
0.7-0.8	109
0.8-0.85	27
0.85-0.9	19
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9252	High Similarity	NPD1653	Approved
0.8671	High Similarity	NPD1613	Approved
0.8671	High Similarity	NPD1612	Clinical (unspecified phase)
0.859	High Similarity	NPD4868	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3027	Phase 3
0.8424	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD5844	Phase 1
0.8392	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2801	Approved
0.8322	Intermediate Similarity	NPD7266	Discontinued
0.8322	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7054	Approved
0.828	Intermediate Similarity	NPD1934	Approved
0.8242	Intermediate Similarity	NPD7472	Approved
0.8221	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6166	Phase 2
0.8221	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1652	Phase 2
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD5402	Approved
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8121	Intermediate Similarity	NPD3818	Discontinued
0.8113	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.8108	Intermediate Similarity	NPD5124	Phase 1
0.8108	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7549	Discontinued
0.8084	Intermediate Similarity	NPD6797	Phase 2
0.8084	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7251	Discontinued
0.8028	Intermediate Similarity	NPD422	Phase 1
0.7988	Intermediate Similarity	NPD7808	Phase 3
0.7963	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD4380	Phase 2
0.7901	Intermediate Similarity	NPD3882	Suspended
0.7891	Intermediate Similarity	NPD4908	Phase 1
0.7885	Intermediate Similarity	NPD1511	Approved
0.7871	Intermediate Similarity	NPD6190	Approved
0.7853	Intermediate Similarity	NPD7075	Discontinued
0.7848	Intermediate Similarity	NPD5403	Approved
0.7805	Intermediate Similarity	NPD6234	Discontinued
0.7798	Intermediate Similarity	NPD7228	Approved
0.7785	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1512	Approved
0.7758	Intermediate Similarity	NPD5494	Approved
0.7746	Intermediate Similarity	NPD1548	Phase 1
0.7722	Intermediate Similarity	NPD5401	Approved
0.7716	Intermediate Similarity	NPD6801	Discontinued
0.7716	Intermediate Similarity	NPD37	Approved
0.7711	Intermediate Similarity	NPD7199	Phase 2
0.7703	Intermediate Similarity	NPD2861	Phase 2
0.7692	Intermediate Similarity	NPD3750	Approved
0.7683	Intermediate Similarity	NPD4965	Approved
0.7683	Intermediate Similarity	NPD4967	Phase 2
0.7683	Intermediate Similarity	NPD4966	Approved
0.7673	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1610	Phase 2
0.7616	Intermediate Similarity	NPD6559	Discontinued
0.7586	Intermediate Similarity	NPD3496	Discontinued
0.7584	Intermediate Similarity	NPD3018	Phase 2
0.7566	Intermediate Similarity	NPD4060	Phase 1
0.7561	Intermediate Similarity	NPD7819	Suspended
0.756	Intermediate Similarity	NPD6232	Discontinued
0.7547	Intermediate Similarity	NPD6799	Approved
0.7546	Intermediate Similarity	NPD7411	Suspended
0.7544	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD230	Phase 1
0.7515	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD3225	Approved
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1549	Phase 2
0.7436	Intermediate Similarity	NPD2935	Discontinued
0.7432	Intermediate Similarity	NPD2982	Phase 2
0.7432	Intermediate Similarity	NPD2983	Phase 2
0.7427	Intermediate Similarity	NPD7473	Discontinued
0.7416	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1091	Approved
0.7407	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6674	Discontinued
0.7403	Intermediate Similarity	NPD447	Suspended
0.7403	Intermediate Similarity	NPD4340	Discontinued
0.7391	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3751	Discontinued
0.7372	Intermediate Similarity	NPD3748	Approved
0.7368	Intermediate Similarity	NPD4625	Phase 3
0.7365	Intermediate Similarity	NPD2981	Phase 2
0.7365	Intermediate Similarity	NPD7768	Phase 2
0.7333	Intermediate Similarity	NPD2797	Approved
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1551	Phase 2
0.7325	Intermediate Similarity	NPD2796	Approved
0.732	Intermediate Similarity	NPD6798	Discontinued
0.732	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4749	Approved
0.7314	Intermediate Similarity	NPD7240	Approved
0.7305	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD919	Approved
0.7273	Intermediate Similarity	NPD6599	Discontinued
0.7267	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1510	Phase 2
0.7261	Intermediate Similarity	NPD7033	Discontinued
0.7256	Intermediate Similarity	NPD3687	Approved
0.7256	Intermediate Similarity	NPD3686	Approved
0.7254	Intermediate Similarity	NPD228	Approved
0.7251	Intermediate Similarity	NPD3787	Discontinued
0.7246	Intermediate Similarity	NPD8455	Phase 2
0.7239	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7212	Phase 2
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7222	Intermediate Similarity	NPD7213	Phase 3
0.7208	Intermediate Similarity	NPD3268	Approved
0.7197	Intermediate Similarity	NPD7097	Phase 1
0.7193	Intermediate Similarity	NPD6959	Discontinued
0.7192	Intermediate Similarity	NPD5536	Phase 2
0.719	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD1933	Approved
0.7178	Intermediate Similarity	NPD7447	Phase 1
0.7172	Intermediate Similarity	NPD6671	Approved
0.717	Intermediate Similarity	NPD5762	Approved
0.717	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5677	Discontinued
0.7125	Intermediate Similarity	NPD2424	Discontinued
0.7119	Intermediate Similarity	NPD7039	Approved
0.7119	Intermediate Similarity	NPD7038	Approved
0.7118	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3749	Approved
0.7115	Intermediate Similarity	NPD1558	Phase 1
0.7108	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1247	Approved
0.7089	Intermediate Similarity	NPD4536	Approved
0.7089	Intermediate Similarity	NPD4538	Approved
0.7089	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5535	Approved
0.7081	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6832	Phase 2
0.7072	Intermediate Similarity	NPD6841	Approved
0.7072	Intermediate Similarity	NPD6843	Phase 3
0.7072	Intermediate Similarity	NPD6842	Approved
0.7066	Intermediate Similarity	NPD4675	Approved
0.7066	Intermediate Similarity	NPD4678	Approved
0.7063	Intermediate Similarity	NPD3540	Phase 1
0.7044	Intermediate Similarity	NPD4308	Phase 3
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7037	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4110	Phase 3
0.7034	Intermediate Similarity	NPD5283	Phase 1
0.7025	Intermediate Similarity	NPD6653	Approved
0.7006	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1240	Approved
0.7006	Intermediate Similarity	NPD4140	Approved
0.7006	Intermediate Similarity	NPD3620	Phase 2
0.7005	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6032	Approved
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD3539	Phase 1
0.7	Intermediate Similarity	NPD5353	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.7	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1203	Approved
0.6987	Remote Similarity	NPD1296	Phase 2
0.6975	Remote Similarity	NPD5177	Phase 3
0.6972	Remote Similarity	NPD290	Approved
0.6972	Remote Similarity	NPD1358	Approved
0.6966	Remote Similarity	NPD7843	Approved
0.6962	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1611	Approved
0.6954	Remote Similarity	NPD1535	Discovery
0.6954	Remote Similarity	NPD3705	Approved
0.6951	Remote Similarity	NPD5058	Phase 3
0.6947	Remote Similarity	NPD7680	Approved
0.6943	Remote Similarity	NPD4062	Phase 3
0.6939	Remote Similarity	NPD7157	Approved
0.6937	Remote Similarity	NPD5588	Approved
0.6937	Remote Similarity	NPD5960	Phase 3
0.6933	Remote Similarity	NPD8166	Discontinued
0.6933	Remote Similarity	NPD1778	Approved
0.6933	Remote Similarity	NPD4626	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data