NPASS Compound

Natural Product: NPC192546

Natural Product ID	NPC192546
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XWVVPZWKCNXREE-VSQYQUPVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14036559
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 76 80 0 0 0 0 0 0 0 0999 V2000 5.1674 0.9200 3.0522 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8635 0.1587 2.0238 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8638 -0.0059 0.9473 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1411 0.5058 -0.3006 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0698 -0.4697 -0.6235 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2665 0.0232 -1.7705 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0652 0.8575 -1.5480 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2594 0.5101 -0.2757 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6785 1.6121 0.6718 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8199 -0.8063 0.0666 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0904 -1.8806 -0.0976 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2978 -1.8865 -0.6209 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9466 -0.6424 -0.1409 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4458 -0.6254 -0.4102 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8412 -0.6990 -1.8192 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9673 -1.9527 0.2001 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4750 -1.9282 0.2979 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0855 -0.7403 0.9037 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4795 0.5769 0.5007 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1144 1.1896 -0.6900 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7520 1.5222 1.6795 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0050 0.4176 0.4661 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3117 1.7425 0.4470 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8070 1.6090 0.5785 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2152 0.6081 -0.4439 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5901 1.2871 -1.7319 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4458 -0.7083 0.5169 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2253 -0.9746 0.5196 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5611 -0.5478 1.8862 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8686 -1.6301 -1.2175 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8418 -2.7709 -0.7030 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6299 -1.4144 -2.3374 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4952 1.0990 3.8898 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1378 1.4156 3.1026 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7749 0.6057 1.1291 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1115 -1.0683 0.7400 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8475 1.5503 -0.2021 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8850 0.4861 -1.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0611 -0.8397 -2.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9684 0.6566 -2.3993 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3071 1.9394 -1.5912 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4529 0.6814 -2.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7703 1.6987 0.8147 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4539 2.5729 0.1148 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2175 1.6596 1.6303 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4998 -2.8948 0.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3330 -2.0421 -1.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8089 -2.7791 -0.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9116 -0.7515 0.9956 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6823 -1.4390 -2.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0118 -1.1562 -2.4106 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2496 0.2180 -2.2829 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5055 -2.1585 1.1599 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7854 -2.7682 -0.5664 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9862 -2.1560 -0.6582 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7370 -2.8154 0.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1035 -0.8532 2.0127 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4912 0.3842 -1.3882 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5214 1.9416 -1.2063 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0694 1.7202 -0.3944 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8326 1.4038 1.9029 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6414 2.5746 1.3019 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0887 1.3248 2.5213 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7683 0.0393 1.5205 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6626 2.4774 -0.2702 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6100 2.2463 1.4321 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6504 1.2172 1.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4562 2.6380 0.4073 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1605 2.1250 -1.8632 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5395 0.6944 -2.6366 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5509 1.7617 -1.6972 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7902 -1.6140 0.7160 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4516 -2.0957 0.5416 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7096 -1.4159 2.6197 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7630 0.0141 2.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0878 -2.1553 -2.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 18 27 1 0 10 28 1 0 28 29 1 0 5 30 1 6 30 31 2 0 30 32 1 0 29 2 1 0 28 5 1 0 25 8 1 0 25 13 1 0 22 14 1 0 1 33 1 0 1 34 1 0 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 6 39 1 0 6 40 1 0 7 41 1 0 7 42 1 0 9 43 1 0 9 44 1 0 9 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 1 15 50 1 0 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 1 20 58 1 0 20 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 1 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 26 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 28 73 1 1 29 74 1 0 29 75 1 0 32 76 1 0 M END

Standard InCHIKey	XWVVPZWKCNXREE-VSQYQUPVSA-N
Standard InCHI	InChI=1S/C29H44O3/c1-18-9-14-29(24(31)32)16-15-27(5)19(20(29)17-18)7-8-22-26(4)12-11-23(30)25(2,3)21(26)10-13-28(22,27)6/h7,20-23,30H,1,8-17H2,2-6H3,(H,31,32)/t20-,21-,22+,23-,26-,27+,28+,29-/m0/s1
SMILES	C=C1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.33	Volume:	485.819 ? Van der Waals volume.
Dense:	0.906	LogP:	3.767 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.301 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.95 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	28.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.443	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.771	Fsp³:	0.828
MCE-18:	100.528 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.817	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.021 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.432	Promiscuous compounds:	0.109

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.512	MDCK Permeability:	-5.096
Pgp-inhibitor:	0.001	Pgp-substrate:	0.076
PAMPA:	0.995 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.893	30% Bioavailability (F30%):	0.622
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.969	MRP1:	0.988
Plasma Protein Binding (PPB):	97.088%	Volume Distribution (VD):	-0.513
Fu:	3.224% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.697	BCRP inhibitor:	0.249
BSEP inhibitor:	0.682

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.022	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.101	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.056
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.003
HLM stability:	0.006 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.93

Half-life (T1/2):

0.63

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.06
Human Hepatotoxicity (H-HT):	0.64	Drug-induced Liver Injury (DILI):	0.719
AMES Toxicity:	0.34	Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.48	Skin Sensitization:	0.949
Carcinogencity:	0.902	Eye Corrosion:	0.058
Eye Irritation:	0.8	Respiratory Toxicity:	0.927
Drug-induced Neurotoxicity:	0.13	Ototoxicity:	0.574
Hematotoxicity:	0.431	Drug-induced Nephrotoxicity:	0.84
Genotoxicity:	0.731	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.207	Hek293 Cytotoxicity:	0.158
BCF:	1.234 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.834 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.346 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.745 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	roots	Whitessence Srl, Viterbo, Italy	2005-OCT	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	DingXi, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	LanZhou, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15265	Paeonia rockii	Species	Paeoniaceae	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	Organism Name	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

Molecular-level activity

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

In vitro activity

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

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC192546 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	21973
0.1-0.2	23089
0.2-0.3	3695
0.3-0.4	703
0.4-0.5	274
0.5-0.6	77
0.6-0.7	27
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8594	High Similarity	NPC130520
0.7812	Intermediate Similarity	NPC480946
0.7812	Intermediate Similarity	NPC130577
0.7812	Intermediate Similarity	NPC142415
0.7812	Intermediate Similarity	NPC102683
0.7692	Intermediate Similarity	NPC182797
0.7692	Intermediate Similarity	NPC52169
0.7692	Intermediate Similarity	NPC488562
0.7015	Intermediate Similarity	NPC187722
0.6957	Remote Similarity	NPC293564
0.6912	Remote Similarity	NPC51700
0.6912	Remote Similarity	NPC88716
0.6912	Remote Similarity	NPC68160
0.6912	Remote Similarity	NPC606443
0.6714	Remote Similarity	NPC202728
0.6714	Remote Similarity	NPC158059
0.6667	Remote Similarity	NPC270768
0.6667	Remote Similarity	NPC59263
0.6667	Remote Similarity	NPC210106
0.6667	Remote Similarity	NPC121798
0.6667	Remote Similarity	NPC234346
0.6667	Remote Similarity	NPC116457
0.6522	Remote Similarity	NPC198664
0.6479	Remote Similarity	NPC298554
0.6447	Remote Similarity	NPC478836
0.6301	Remote Similarity	NPC127689
0.625	Remote Similarity	NPC228784
0.625	Remote Similarity	NPC324341
0.625	Remote Similarity	NPC601810
0.6197	Remote Similarity	NPC171203
0.6197	Remote Similarity	NPC307426
0.6197	Remote Similarity	NPC98442
0.6197	Remote Similarity	NPC242468
0.6143	Remote Similarity	NPC477872
0.6056	Remote Similarity	NPC274330
0.6053	Remote Similarity	NPC474727
0.5972	Remote Similarity	NPC7260
0.5972	Remote Similarity	NPC210037
0.5972	Remote Similarity	NPC229281
0.5972	Remote Similarity	NPC120968
0.5972	Remote Similarity	NPC64872
0.5972	Remote Similarity	NPC84319
0.5972	Remote Similarity	NPC25906
0.5972	Remote Similarity	NPC52021
0.5972	Remote Similarity	NPC227467
0.5972	Remote Similarity	NPC273621
0.5972	Remote Similarity	NPC112866
0.5972	Remote Similarity	NPC599947
0.5949	Remote Similarity	NPC603645
0.589	Remote Similarity	NPC61543
0.589	Remote Similarity	NPC293048
0.589	Remote Similarity	NPC225585
0.589	Remote Similarity	NPC472149
0.5811	Remote Similarity	NPC136697
0.5789	Remote Similarity	NPC174663
0.5753	Remote Similarity	NPC282616
0.5753	Remote Similarity	NPC275809
0.5733	Remote Similarity	NPC191412
0.5733	Remote Similarity	NPC114159
0.5733	Remote Similarity	NPC6818
0.5676	Remote Similarity	NPC88116
0.5676	Remote Similarity	NPC158141
0.5658	Remote Similarity	NPC25299
0.5658	Remote Similarity	NPC481322
0.5616	Remote Similarity	NPC610937
0.56	Remote Similarity	NPC29765
0.5584	Remote Similarity	NPC187933
0.5541	Remote Similarity	NPC195019
0.5526	Remote Similarity	NPC263393
0.5526	Remote Similarity	NPC91010
0.5506	Remote Similarity	NPC488215
0.5493	Remote Similarity	NPC604575
0.5467	Remote Similarity	NPC231063
0.5467	Remote Similarity	NPC18872
0.5467	Remote Similarity	NPC282395
0.5467	Remote Similarity	NPC130278
0.5467	Remote Similarity	NPC290614
0.5467	Remote Similarity	NPC110308
0.5467	Remote Similarity	NPC609452
0.5325	Remote Similarity	NPC118519
0.5325	Remote Similarity	NPC474963
0.5263	Remote Similarity	NPC106112
0.5263	Remote Similarity	NPC261935
0.5263	Remote Similarity	NPC71074
0.5263	Remote Similarity	NPC37221
0.5263	Remote Similarity	NPC481360
0.5263	Remote Similarity	NPC605937
0.5217	Remote Similarity	NPC290598
0.5217	Remote Similarity	NPC27765
0.5217	Remote Similarity	NPC30590
0.5217	Remote Similarity	NPC122418
0.5217	Remote Similarity	NPC491014
0.5211	Remote Similarity	NPC101475
0.5195	Remote Similarity	NPC259733
0.5195	Remote Similarity	NPC158371
0.5195	Remote Similarity	NPC207922
0.5195	Remote Similarity	NPC200752
0.5195	Remote Similarity	NPC120840
0.519	Remote Similarity	NPC20235
0.519	Remote Similarity	NPC299996
0.519	Remote Similarity	NPC222047
0.5176	Remote Similarity	NPC204407
0.5139	Remote Similarity	NPC235341
0.5132	Remote Similarity	NPC37038
0.5128	Remote Similarity	NPC610635
0.5122	Remote Similarity	NPC188833
0.5116	Remote Similarity	NPC283849
0.5116	Remote Similarity	NPC28198
0.5116	Remote Similarity	NPC476123
0.5116	Remote Similarity	NPC606107
0.5109	Remote Similarity	NPC198621
0.5109	Remote Similarity	NPC216940
0.5065	Remote Similarity	NPC38754

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC192546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6590
0.1-0.2	2495
0.2-0.3	57
0.3-0.4	5
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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