NPASS Compound

Structure

CID162169 OpenBabel06191715532D 56 62 0 0 1 0 0 0 0 0999 V2000 -6.1519 1.6157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1406 -2.2857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4037 2.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8556 1.9082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3503 1.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1406 -1.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2082 1.4455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0471 1.2069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9929 -2.7777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3367 2.7230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1765 1.1960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4438 0.0652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9929 -0.8095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9458 0.7940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1596 -0.1666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7679 -1.0693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9203 -1.5695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1406 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8451 -2.2857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0742 2.0715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3390 -0.3436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8451 -1.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8788 1.1070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6455 -0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6518 -1.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0593 -1.4759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4195 -1.6450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9903 0.2297 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7969 -0.8244 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0106 0.1362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7419 1.8184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1576 -1.2547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2286 1.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1414 -0.1090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8487 1.7777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9929 -3.7618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5321 3.6875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3018 1.6470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0358 -0.1816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6974 -2.7777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0072 2.3845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 -1.3233 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6974 -0.8095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6163 0.4555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6148 -0.6727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6023 -2.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4510 -2.3787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1571 -2.2965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3128 2.6200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8358 -2.1847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0148 2.4997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1601 1.5751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8120 2.1403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3560 -0.6839 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 -0.6189 1.0389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 8 1 0 0 0 0 2 6 2 0 0 0 0 2 9 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 4 53 1 0 0 0 0 5 12 1 0 0 0 0 5 31 1 0 0 0 0 6 13 1 0 0 0 0 6 32 1 0 0 0 0 7 14 1 0 0 0 0 7 33 1 0 0 0 0 8 18 2 0 0 0 0 8 35 1 0 0 0 0 9 19 2 0 0 0 0 9 36 1 0 0 0 0 10 20 2 0 0 0 0 10 37 1 0 0 0 0 11 28 1 0 0 0 0 11 38 1 1 0 0 0 12 13 1 0 0 0 0 12 21 2 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 23 2 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 34 1 0 0 0 0 17 25 2 0 0 0 0 17 26 1 0 0 0 0 18 21 1 0 0 0 0 18 39 1 0 0 0 0 19 22 1 0 0 0 0 19 40 1 0 0 0 0 20 23 1 0 0 0 0 20 41 1 0 0 0 0 21 42 1 0 0 0 0 22 43 1 0 0 0 0 23 44 1 0 0 0 0 24 27 2 0 0 0 0 24 45 1 0 0 0 0 25 27 1 0 0 0 0 25 46 1 0 0 0 0 26 29 1 0 0 0 0 26 47 1 1 0 0 0 27 48 1 0 0 0 0 28 30 1 0 0 0 0 28 54 1 6 0 0 0 29 30 1 0 0 0 0 29 55 1 6 0 0 0 30 56 1 6 0 0 0 31 49 2 0 0 0 0 31 53 1 0 0 0 0 32 50 2 0 0 0 0 32 54 1 0 0 0 0 33 51 2 0 0 0 0 33 56 1 0 0 0 0 34 52 2 0 0 0 0 34 55 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	784.08
Volume:	687.926
LogP:	0.856
LogD:	0.262
LogS:	-3.585
# Rotatable Bonds:	1
TPSA:	388.42
# H-Bond Aceptor:	22
# H-Bond Donor:	14
# Rings:	8
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.07
Synthetic Accessibility Score:	6.559
Fsp3:	0.176
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.137
MDCK Permeability:	3.980340807174798e-06
Pgp-inhibitor:	0.165
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	86.63855743408203%
Volume Distribution (VD):	0.427
Pgp-substrate:	41.40852355957031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.023
CYP2C9-inhibitor:	0.337
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	5.416
Half-life (T1/2):	0.941

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.322
Drug-inuced Liver Injury (DILI):	0.994
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.933
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.886
Respiratory Toxicity:	0.002

Download Data

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

Natural Product: NPC162169

Natural Product ID:	NPC162169
*Common Name:**	Casuariin
IUPAC Name:	n.a.
Synonyms:	Casuariin
Standard InCHIKey:	CHBITXAMNKHJCR-JNUHSSLSSA-N
Standard InCHI:	InChI=1S/C34H24O22/c35-8-1-5-12(21(42)18(8)39)13-6(2-9(36)19(40)22(13)43)32(50)54-28(11(38)4-53-31(5)49)30-29-26(47)17-16(34(52)55-29)15(24(45)27(48)25(17)46)14-7(33(51)56-30)3-10(37)20(41)23(14)44/h1-3,11,26,28-30,35-48H,4H2/t11-,26-,28-,29+,30+/m1/s1
SMILES:	c1c2c(-c3c(cc(c(c3O)O)O)C(=O)O[C@H]([C@@H](COC2=O)O)[C@H]2[C@@H]3[C@@H](c4c(c(-c5c(cc(c(c5O)O)O)C(=O)O2)c(c(c4O)O)O)C(=O)O3)O)c(c(c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509562
PubChem CID:	14035442
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF00579992]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.foodchem.2010.03.088]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/np50028a032]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10993241]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	roots	n.a.	n.a.	PMID[19691309]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466012]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28245113]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31738062]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4013523]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[8759159]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759159]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834152]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	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	3
Ki	2
Others	7

Activity Type	# Activity
Individual Protein	5
Others	1
Tissue	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2533	Individual Protein	Coagulation factor X	Homo sapiens	IC50	=	720.0	nM	PMID[493250]
NPT2533	Individual Protein	Coagulation factor X	Homo sapiens	Ki	=	450.0	nM	PMID[493250]
NPT2534	Individual Protein	Thrombin	Bos taurus	IC50	=	59.0	nM	PMID[493250]
NPT2534	Individual Protein	Thrombin	Bos taurus	IC50	=	280.0	nM	PMID[493250]
NPT2534	Individual Protein	Thrombin	Bos taurus	Ki	=	980.0	nM	PMID[493250]
NPT2	Others	Unspecified		Ratio Ki	=	1.2	n.a.	PMID[493250]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	APTT	>	300.0	s	PMID[493250]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	TT	>	300.0	s	PMID[493250]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	PT	>	300.0	s	PMID[493250]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	APTT	=	72.3	s	PMID[493250]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	TT	=	12.3	s	PMID[493250]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	PT	=	13.6	s	PMID[493250]

☑ 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 NPC162169 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	405
0.1-0.2	1699
0.2-0.3	3877
0.3-0.4	9148
0.4-0.5	9533
0.5-0.6	4374
0.6-0.7	6581
0.7-0.8	6645
0.8-0.85	353
0.85-0.9	64
0.9-0.95	11
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC166851
0.9936	High Similarity	NPC317671
0.9936	High Similarity	NPC142707
0.9936	High Similarity	NPC49983
0.9936	High Similarity	NPC26536
0.9873	High Similarity	NPC217781
0.9623	High Similarity	NPC31034
0.9437	High Similarity	NPC175793
0.9383	High Similarity	NPC47521
0.9379	High Similarity	NPC311389
0.9379	High Similarity	NPC470271
0.9337	High Similarity	NPC125352
0.9264	High Similarity	NPC470272
0.9259	High Similarity	NPC261411
0.9259	High Similarity	NPC43918
0.9259	High Similarity	NPC190204
0.913	High Similarity	NPC14030
0.913	High Similarity	NPC291957
0.9119	High Similarity	NPC474010
0.9119	High Similarity	NPC135222
0.9118	High Similarity	NPC237202
0.9091	High Similarity	NPC65333
0.9074	High Similarity	NPC470898
0.9064	High Similarity	NPC269046
0.9053	High Similarity	NPC129533
0.9053	High Similarity	NPC123259
0.9042	High Similarity	NPC472723
0.8976	High Similarity	NPC100251
0.8938	High Similarity	NPC239019
0.8938	High Similarity	NPC247629
0.8935	High Similarity	NPC80956
0.8922	High Similarity	NPC98583
0.891	High Similarity	NPC142528
0.8882	High Similarity	NPC238419
0.8882	High Similarity	NPC172419
0.8846	High Similarity	NPC268366
0.8779	High Similarity	NPC231254
0.8773	High Similarity	NPC24627
0.8772	High Similarity	NPC8940
0.8758	High Similarity	NPC203757
0.8743	High Similarity	NPC264302
0.8728	High Similarity	NPC261623
0.8728	High Similarity	NPC111490
0.8728	High Similarity	NPC112380
0.8728	High Similarity	NPC469650
0.872	High Similarity	NPC266365
0.8712	High Similarity	NPC318826
0.8712	High Similarity	NPC114791
0.8712	High Similarity	NPC210501
0.8712	High Similarity	NPC141331
0.8712	High Similarity	NPC104222
0.8706	High Similarity	NPC297574
0.8704	High Similarity	NPC250436
0.8704	High Similarity	NPC291948
0.8704	High Similarity	NPC300845
0.8704	High Similarity	NPC134925
0.8704	High Similarity	NPC88803
0.8704	High Similarity	NPC104983
0.8683	High Similarity	NPC107009
0.8678	High Similarity	NPC65489
0.8675	High Similarity	NPC471788
0.8663	High Similarity	NPC117668
0.8663	High Similarity	NPC208797
0.8663	High Similarity	NPC53680
0.8659	High Similarity	NPC24164
0.8655	High Similarity	NPC265380
0.8655	High Similarity	NPC471789
0.8654	High Similarity	NPC226738
0.8654	High Similarity	NPC190587
0.8654	High Similarity	NPC22176
0.8654	High Similarity	NPC121573
0.865	High Similarity	NPC289322
0.865	High Similarity	NPC38779
0.865	High Similarity	NPC160512
0.865	High Similarity	NPC68324
0.865	High Similarity	NPC114179
0.865	High Similarity	NPC156818
0.8644	High Similarity	NPC477082
0.8636	High Similarity	NPC97924
0.8636	High Similarity	NPC471091
0.8636	High Similarity	NPC40078
0.8634	High Similarity	NPC61152
0.8634	High Similarity	NPC3746
0.8634	High Similarity	NPC205037
0.8634	High Similarity	NPC16024
0.8634	High Similarity	NPC44260
0.8629	High Similarity	NPC173872
0.8629	High Similarity	NPC119094
0.8629	High Similarity	NPC477083
0.8629	High Similarity	NPC477081
0.8625	High Similarity	NPC252979
0.8605	High Similarity	NPC185275
0.8605	High Similarity	NPC198902
0.8598	High Similarity	NPC471750
0.8598	High Similarity	NPC87317
0.8596	High Similarity	NPC67629
0.8596	High Similarity	NPC79736
0.8589	High Similarity	NPC318432
0.858	High Similarity	NPC43872
0.858	High Similarity	NPC291510
0.858	High Similarity	NPC472720
0.858	High Similarity	NPC116850
0.858	High Similarity	NPC472721
0.858	High Similarity	NPC472724
0.858	High Similarity	NPC469652
0.858	High Similarity	NPC31208
0.858	High Similarity	NPC160543
0.858	High Similarity	NPC180768
0.858	High Similarity	NPC197188
0.858	High Similarity	NPC144801
0.858	High Similarity	NPC238672
0.858	High Similarity	NPC93065
0.8571	High Similarity	NPC269625
0.8571	High Similarity	NPC469649
0.8571	High Similarity	NPC227485
0.8571	High Similarity	NPC260521
0.8571	High Similarity	NPC473818
0.8556	High Similarity	NPC174140
0.8554	High Similarity	NPC476371
0.8554	High Similarity	NPC476372
0.8553	High Similarity	NPC81835
0.8547	High Similarity	NPC267549
0.8545	High Similarity	NPC53889
0.8539	High Similarity	NPC476358
0.8529	High Similarity	NPC262580
0.8529	High Similarity	NPC212038
0.8529	High Similarity	NPC289396
0.8529	High Similarity	NPC81332
0.8529	High Similarity	NPC271848
0.8523	High Similarity	NPC158214
0.8523	High Similarity	NPC240200
0.8523	High Similarity	NPC7839
0.8523	High Similarity	NPC223534
0.8523	High Similarity	NPC290289
0.8523	High Similarity	NPC142291
0.8503	High Similarity	NPC67959
0.8497	Intermediate Similarity	NPC324742
0.8494	Intermediate Similarity	NPC139540
0.8494	Intermediate Similarity	NPC177100
0.8485	Intermediate Similarity	NPC267627
0.8485	Intermediate Similarity	NPC37502
0.8485	Intermediate Similarity	NPC40702
0.848	Intermediate Similarity	NPC34436
0.848	Intermediate Similarity	NPC166674
0.848	Intermediate Similarity	NPC46640
0.848	Intermediate Similarity	NPC263119
0.848	Intermediate Similarity	NPC219600
0.848	Intermediate Similarity	NPC473550
0.8475	Intermediate Similarity	NPC187632
0.8475	Intermediate Similarity	NPC201814
0.8471	Intermediate Similarity	NPC181778
0.8471	Intermediate Similarity	NPC476365
0.8466	Intermediate Similarity	NPC281703
0.8466	Intermediate Similarity	NPC105591
0.8466	Intermediate Similarity	NPC125487
0.8457	Intermediate Similarity	NPC228662
0.8444	Intermediate Similarity	NPC189312
0.8443	Intermediate Similarity	NPC473445
0.8438	Intermediate Similarity	NPC43123
0.8438	Intermediate Similarity	NPC476463
0.8438	Intermediate Similarity	NPC120621
0.8438	Intermediate Similarity	NPC248257
0.8434	Intermediate Similarity	NPC476373
0.8424	Intermediate Similarity	NPC247713
0.8421	Intermediate Similarity	NPC472454
0.8421	Intermediate Similarity	NPC257667
0.8421	Intermediate Similarity	NPC477836
0.8421	Intermediate Similarity	NPC186847
0.8412	Intermediate Similarity	NPC475212
0.8412	Intermediate Similarity	NPC95421
0.8412	Intermediate Similarity	NPC198125
0.8405	Intermediate Similarity	NPC474656
0.8402	Intermediate Similarity	NPC320741
0.8402	Intermediate Similarity	NPC207575
0.8402	Intermediate Similarity	NPC224851
0.8402	Intermediate Similarity	NPC477835
0.8402	Intermediate Similarity	NPC171985
0.8402	Intermediate Similarity	NPC9309
0.8402	Intermediate Similarity	NPC13481
0.84	Intermediate Similarity	NPC132111
0.8397	Intermediate Similarity	NPC105525
0.8397	Intermediate Similarity	NPC225036
0.8397	Intermediate Similarity	NPC75763
0.8397	Intermediate Similarity	NPC12218
0.8395	Intermediate Similarity	NPC140151
0.8393	Intermediate Similarity	NPC291977
0.8393	Intermediate Similarity	NPC469651
0.8393	Intermediate Similarity	NPC45943
0.8385	Intermediate Similarity	NPC221352
0.8385	Intermediate Similarity	NPC92117
0.8385	Intermediate Similarity	NPC42464
0.8373	Intermediate Similarity	NPC94220
0.8373	Intermediate Similarity	NPC24339
0.8373	Intermediate Similarity	NPC7543
0.8373	Intermediate Similarity	NPC166456
0.8373	Intermediate Similarity	NPC98083
0.8364	Intermediate Similarity	NPC165483
0.8363	Intermediate Similarity	NPC313304
0.8362	Intermediate Similarity	NPC179947
0.8354	Intermediate Similarity	NPC178134

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 NPC162169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	959
0.2-0.3	1937
0.3-0.4	2816
0.4-0.5	1778
0.5-0.6	925
0.6-0.7	274
0.7-0.8	97
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD7993	Clinical (unspecified phase)
0.8704	High Similarity	NPD4868	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD5844	Phase 1
0.8354	Intermediate Similarity	NPD1465	Phase 2
0.8225	Intermediate Similarity	NPD6232	Discontinued
0.8166	Intermediate Similarity	NPD6959	Discontinued
0.8081	Intermediate Similarity	NPD7473	Discontinued
0.8045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6166	Phase 2
0.8023	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4380	Phase 2
0.7919	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6190	Approved
0.7898	Intermediate Similarity	NPD230	Phase 1
0.7865	Intermediate Similarity	NPD8313	Approved
0.7865	Intermediate Similarity	NPD8312	Approved
0.7829	Intermediate Similarity	NPD7228	Approved
0.7811	Intermediate Similarity	NPD7819	Suspended
0.7805	Intermediate Similarity	NPD7390	Discontinued
0.7801	Intermediate Similarity	NPD8151	Discontinued
0.776	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD1934	Approved
0.774	Intermediate Similarity	NPD7074	Phase 3
0.774	Intermediate Similarity	NPD7472	Approved
0.7735	Intermediate Similarity	NPD8150	Discontinued
0.7733	Intermediate Similarity	NPD6234	Discontinued
0.7727	Intermediate Similarity	NPD3818	Discontinued
0.7719	Intermediate Similarity	NPD7768	Phase 2
0.7709	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD8455	Phase 2
0.7697	Intermediate Similarity	NPD6797	Phase 2
0.7684	Intermediate Similarity	NPD7054	Approved
0.7674	Intermediate Similarity	NPD7075	Discontinued
0.7654	Intermediate Similarity	NPD7251	Discontinued
0.7647	Intermediate Similarity	NPD37	Approved
0.7616	Intermediate Similarity	NPD4967	Phase 2
0.7616	Intermediate Similarity	NPD4966	Approved
0.7616	Intermediate Similarity	NPD4965	Approved
0.7611	Intermediate Similarity	NPD7808	Phase 3
0.7593	Intermediate Similarity	NPD5408	Approved
0.7593	Intermediate Similarity	NPD5405	Approved
0.7593	Intermediate Similarity	NPD5404	Approved
0.7593	Intermediate Similarity	NPD5406	Approved
0.7588	Intermediate Similarity	NPD7411	Suspended
0.7582	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3749	Approved
0.7572	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5494	Approved
0.7471	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6559	Discontinued
0.7459	Intermediate Similarity	NPD7240	Approved
0.7457	Intermediate Similarity	NPD3817	Phase 2
0.7443	Intermediate Similarity	NPD7199	Phase 2
0.744	Intermediate Similarity	NPD2534	Approved
0.744	Intermediate Similarity	NPD2532	Approved
0.744	Intermediate Similarity	NPD2533	Approved
0.7414	Intermediate Similarity	NPD3882	Suspended
0.741	Intermediate Similarity	NPD8166	Discontinued
0.741	Intermediate Similarity	NPD3750	Approved
0.7391	Intermediate Similarity	NPD943	Approved
0.7381	Intermediate Similarity	NPD1511	Approved
0.7375	Intermediate Similarity	NPD3764	Approved
0.7363	Intermediate Similarity	NPD7685	Pre-registration
0.7356	Intermediate Similarity	NPD5402	Approved
0.7353	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7266	Discontinued
0.7333	Intermediate Similarity	NPD3751	Discontinued
0.732	Intermediate Similarity	NPD8320	Phase 1
0.732	Intermediate Similarity	NPD8319	Approved
0.7317	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD9269	Phase 2
0.7303	Intermediate Similarity	NPD3787	Discontinued
0.7302	Intermediate Similarity	NPD6535	Approved
0.7302	Intermediate Similarity	NPD6534	Approved
0.7294	Intermediate Similarity	NPD1512	Approved
0.7289	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7700	Phase 2
0.7277	Intermediate Similarity	NPD7699	Phase 2
0.7268	Intermediate Similarity	NPD7435	Discontinued
0.7263	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6776	Approved
0.7202	Intermediate Similarity	NPD6781	Approved
0.7202	Intermediate Similarity	NPD7003	Approved
0.7202	Intermediate Similarity	NPD6782	Approved
0.7202	Intermediate Similarity	NPD6778	Approved
0.7202	Intermediate Similarity	NPD6777	Approved
0.7202	Intermediate Similarity	NPD6780	Approved
0.7202	Intermediate Similarity	NPD4628	Phase 3
0.7202	Intermediate Similarity	NPD6779	Approved
0.7186	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1549	Phase 2
0.7186	Intermediate Similarity	NPD7783	Phase 2
0.7178	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1613	Approved
0.7151	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7136	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7874	Approved
0.7135	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7229	Phase 3
0.711	Intermediate Similarity	NPD1653	Approved
0.7108	Intermediate Similarity	NPD3748	Approved
0.7108	Intermediate Similarity	NPD1510	Phase 2
0.7092	Intermediate Similarity	NPD7698	Approved
0.7092	Intermediate Similarity	NPD7697	Approved
0.7092	Intermediate Similarity	NPD7680	Approved
0.7092	Intermediate Similarity	NPD7696	Phase 3
0.7076	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6799	Approved
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7069	Intermediate Similarity	NPD3226	Approved
0.7068	Intermediate Similarity	NPD6212	Phase 3
0.7068	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6213	Phase 3
0.7066	Intermediate Similarity	NPD2935	Discontinued
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7051	Intermediate Similarity	NPD9268	Approved
0.7049	Intermediate Similarity	NPD7177	Discontinued
0.7035	Intermediate Similarity	NPD7701	Phase 2
0.7035	Intermediate Similarity	NPD5401	Approved
0.7029	Intermediate Similarity	NPD6599	Discontinued
0.7017	Intermediate Similarity	NPD5710	Approved
0.7017	Intermediate Similarity	NPD5711	Approved
0.6994	Remote Similarity	NPD3027	Phase 3
0.6984	Remote Similarity	NPD8434	Phase 2
0.6975	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6823	Phase 2
0.6944	Remote Similarity	NPD919	Approved
0.6933	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7801	Approved
0.6901	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6273	Approved
0.6885	Remote Similarity	NPD3926	Phase 2
0.6885	Remote Similarity	NPD5242	Approved
0.6875	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5353	Approved
0.6867	Remote Similarity	NPD1240	Approved
0.6864	Remote Similarity	NPD2796	Approved
0.6857	Remote Similarity	NPD920	Approved
0.6853	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2346	Discontinued
0.6789	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1607	Approved
0.678	Remote Similarity	NPD3455	Phase 2
0.6776	Remote Similarity	NPD1247	Approved
0.6772	Remote Similarity	NPD9545	Approved
0.6766	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1551	Phase 2
0.6755	Remote Similarity	NPD5953	Discontinued
0.6748	Remote Similarity	NPD1470	Approved
0.6744	Remote Similarity	NPD2800	Approved
0.6743	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7286	Phase 2
0.6736	Remote Similarity	NPD4287	Approved
0.6727	Remote Similarity	NPD4908	Phase 1
0.6705	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7008	Discontinued
0.6685	Remote Similarity	NPD4288	Approved
0.6684	Remote Similarity	NPD7549	Discontinued
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.6647	Remote Similarity	NPD6798	Discontinued
0.6647	Remote Similarity	NPD1243	Approved
0.6647	Remote Similarity	NPD6674	Discontinued
0.6646	Remote Similarity	NPD1164	Approved
0.6629	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5124	Phase 1
0.6627	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD447	Suspended
0.6618	Remote Similarity	NPD7585	Approved
0.6611	Remote Similarity	NPD6386	Approved
0.6611	Remote Similarity	NPD6385	Approved
0.6608	Remote Similarity	NPD2799	Discontinued
0.6605	Remote Similarity	NPD1201	Approved
0.6588	Remote Similarity	NPD6651	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