NPASS Compound

Structure

NPC201551 OpenBabel06302215332D 56 63 0 0 1 0 0 0 0 0999 V2000 2.5725 -7.7168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5725 -6.7266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7150 -6.2315 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7150 -5.2414 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5725 -4.7463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4300 -5.2414 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4300 -6.2315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2875 -4.7463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2875 -3.7561 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4300 -3.2611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5725 -3.7561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4300 -2.2709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2875 -1.7758 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1450 -2.2709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1450 -3.2611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0025 -3.7561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0025 -4.7463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2875 -0.7856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4300 -0.2906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5725 -0.7856 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5725 -1.7758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7150 -0.2906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7150 0.6996 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5725 1.1947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4300 0.6996 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2875 1.1947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1450 0.6996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8575 1.1947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.6996 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6059 1.0494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2117 0.6996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2117 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9268 0.9902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6059 -0.3498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6059 -1.0494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2117 -1.3992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8176 -1.0494 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8176 -0.3498 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2288 0.2162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8942 0.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5596 0.2162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3645 0.6743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1452 0.2162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1452 -0.6995 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0557 -0.6995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5596 -0.6995 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5596 -1.6154 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3403 -2.0735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1452 -1.6154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8942 -1.8316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2288 -1.6154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6468 -2.4165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8575 -4.7463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.2414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8575 -6.7266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 4 1 0 0 0 0 3 56 1 1 0 0 0 4 5 1 0 0 0 0 4 54 1 6 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 6 0 0 0 9 8 1 6 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 11 1 1 0 0 0 10 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 1 0 0 0 14 15 1 0 0 0 0 15 16 1 1 0 0 0 16 17 1 0 0 0 0 19 18 1 6 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 21 1 1 0 0 0 20 22 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 23 28 1 1 0 0 0 24 25 1 0 0 0 0 25 26 1 1 0 0 0 26 27 1 0 0 0 0 29 28 1 6 0 0 0 29 30 1 0 0 0 0 29 53 1 0 0 0 0 30 31 1 0 0 0 0 31 32 1 0 0 0 0 32 38 1 0 0 0 0 32 33 1 6 0 0 0 32 34 1 0 0 0 0 34 35 2 0 0 0 0 34 53 1 0 0 0 0 35 36 1 0 0 0 0 37 36 1 1 0 0 0 37 38 1 0 0 0 0 37 51 1 0 0 0 0 38 39 1 6 0 0 0 39 40 1 0 0 0 0 40 41 1 0 0 0 0 41 42 2 0 0 0 0 42 43 1 0 0 0 0 43 44 1 0 0 0 0 44 49 1 0 0 0 0 44 45 1 6 0 0 0 44 46 1 0 0 0 0 46 41 1 1 0 0 0 46 47 1 0 0 0 0 47 48 1 1 0 0 0 47 50 1 0 0 0 0 48 49 1 0 0 0 0 50 51 1 0 0 0 0 51 52 2 0 0 0 0 54 55 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	792.43
Volume:	781.69
LogP:	4.693
LogD:	3.369
LogS:	-5.647
# Rotatable Bonds:	9
TPSA:	148.06
# H-Bond Aceptor:	14
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	6.652
Fsp3:	0.881
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.007
MDCK Permeability:	0.00021625583758577704
Pgp-inhibitor:	0.019
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	72.82831573486328%
Volume Distribution (VD):	0.716
Pgp-substrate:	7.249255657196045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.852
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.709
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.719
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	2.998
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.926
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.866
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.542
Carcinogencity:	0.253
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.413

Download Data

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

Natural Product: NPC201551

Natural Product ID:	NPC201551
*Common Name:**	QIUXXAOVQHVQQH-ZPPFTQKESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QIUXXAOVQHVQQH-ZPPFTQKESA-N
Standard InCHI:	InChI=1S/C42H64O14/c1-21-37(43)29(45-6)16-34(50-21)55-39-23(3)52-35(18-31(39)47-8)56-38-22(2)51-33(17-30(38)46-7)53-26-13-14-41(4)25(15-26)10-11-27-28(41)12-9-24-19-48-42(5)36(24)32(20-49-42)54-40(27)44/h10,19,21-23,26-39,43H,9,11-18,20H2,1-8H3/t21-,22-,23-,26+,27-,28+,29-,30-,31-,32+,33+,34+,35+,36+,37-,38-,39-,41+,42-/m1/s1
SMILES:	C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]1[C@@H](C)O[C@H](C[C@H]1OC)O[C@@H]1[C@@H](C)O[C@H](C[C@H]1OC)O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CCC2=CO[C@@]4(C)[C@@H]2[C@H](CO4)OC3=O)C1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO27831	Phakellia flabellata	Species	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00445a028]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11374953]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15056914]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270557]
NPO27850	Trichilia catigua	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[18020420]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19948405]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20415462]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23672042]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24024763]
NPO28158	Polygala fruticosa	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28300	Sorbaria arborea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28507	Hymenoxys grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28300	Sorbaria arborea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28158	Polygala fruticosa	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28176	Russula lepida	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28300	Sorbaria arborea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28543	Alcyonium coralloides	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25330	Maackia floribunda	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10135	Tripteris microcarpa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27906	Philadelphus coronarius	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28507	Hymenoxys grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28282	Turbina corymbosa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11786	Cylindropuntia leptocaulis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28593	Pteris pedata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28071	Dendrobates auratus	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27891	Lethariella sinensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27938	Meliosma wightii	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27831	Phakellia flabellata	Species	Bubaridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28009	Pellina semitubulosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28425	Senecio miser	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28494	Hydroclathrus tenuis	Species	Scytosiphonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28214	Phyllosticta cirsii	Species	Phyllostictaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9245	Ventilago madraspatana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27850	Trichilia catigua	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28574	Oroxylum indicum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28316	Scandix pecten-veneris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28333	Syzygium levinei	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28479	Campanula hypopolia	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28158	Polygala fruticosa	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28651	Othonna tagetes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29373	Trichoplusia ni	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28197	Huperzia selago	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28300	Sorbaria arborea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28461	Crepis czerepanovii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28443	Larix lyallii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27918	Pterocarpus macrocarpus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28404	Chasmanthera dependens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28525	Urginea riparia	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29042	Vincetoxicum atratum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28176	Russula lepida	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28611	Phragmatobia fuliginosa	Species	Erebidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28228	Kielmeyera rubriflora	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27956	Eupatoriastrum nelsonii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27973	Simaba cuneata	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28668	Agave cocui	Species	Asparagaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC201551 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	242
0.1-0.2	1486
0.2-0.3	4958
0.3-0.4	12408
0.4-0.5	9991
0.5-0.6	7404
0.6-0.7	4042
0.7-0.8	1824
0.8-0.85	336
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID

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 NPC201551 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1743
0.2-0.3	4053
0.3-0.4	2140
0.4-0.5	563
0.5-0.6	315
0.6-0.7	104
0.7-0.8	25
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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