NPASS Compound

Natural Product: NPC30846

Natural Product ID	NPC30846
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ONKOOMBIYOLKEL-MCDUMTBSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1629875
PubChem CID	NA
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

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 95 97 0 0 0 0 0 0 0 0999 V2000 -2.0204 -2.3973 -5.3567 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5975 -2.7096 -3.9898 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9059 -2.5024 -2.9036 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3781 -2.7744 -1.4967 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1625 -1.5033 -0.6665 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7289 -1.1944 -0.6358 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0463 -1.0812 0.7012 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2509 -1.8495 0.7027 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2470 -1.4017 -0.2878 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4892 -1.0660 0.0739 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5099 -0.6114 -0.9016 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0610 0.7575 -0.6241 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0572 1.0432 -1.6920 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3286 1.2819 -1.4092 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7626 1.2646 0.0016 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3281 1.5617 -2.4798 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0855 -0.6774 -2.2060 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8386 -1.1852 1.5125 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1126 0.3617 1.0111 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9878 1.0696 1.2679 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0692 0.3771 2.0256 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7801 1.0421 2.8132 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2891 -1.1018 1.8311 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9915 -1.4383 0.5634 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7388 -2.7638 0.6542 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0954 -0.3921 0.3272 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9355 -1.7081 1.7178 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5824 -2.6204 2.3813 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9009 -1.6300 3.0998 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1746 -0.9736 3.4203 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4606 -0.3552 4.5424 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7953 0.2679 4.7227 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4963 -0.2726 5.6564 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2394 2.4129 0.8232 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3282 2.9335 1.3136 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4846 3.2563 -0.0663 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5032 2.8844 -0.9367 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2332 3.8114 -1.6851 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9935 5.1483 -1.5867 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0018 5.5595 -0.7200 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7079 4.6400 0.0107 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2292 6.9251 -0.6339 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7228 6.0555 -2.3326 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3252 0.9566 1.0440 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9601 -3.2568 -3.9853 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8077 -2.2106 -6.0843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3690 -1.4809 -5.2491 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3340 -3.2291 -5.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8938 -2.0915 -3.0556 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7640 -3.6083 -1.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4216 -3.0590 -1.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6236 -0.7034 -1.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4903 -0.2920 -1.2760 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1737 -2.0178 -1.1985 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6492 -1.9604 1.7205 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9723 -2.8999 0.3892 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9811 -1.3398 -1.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3647 -1.3393 -0.7947 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2258 1.5052 -0.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4782 0.8500 0.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7535 1.0626 -2.7257 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8773 1.3139 0.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4393 0.3081 0.4553 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3420 2.1604 0.5407 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2991 1.0873 -2.2878 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4357 2.6492 -2.6002 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9431 1.1054 -3.4388 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4137 -0.0336 -2.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6344 -2.1935 1.9188 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4211 -0.3773 2.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9589 -1.0730 1.6228 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1817 -2.9302 1.6742 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6274 -2.7188 -0.0103 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1448 -3.6311 0.3779 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9470 0.0828 -0.6921 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0616 0.4383 1.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0974 -0.8373 0.3059 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -1.3180 3.9032 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9018 -2.7317 3.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0020 -0.9754 2.6769 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8028 1.1860 4.1007 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6336 -0.4143 4.4705 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9222 0.5858 5.7748 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9556 0.7225 5.6222 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7826 -1.0901 5.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0641 -0.1893 6.6467 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7027 1.8460 -1.1066 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0169 3.4763 -2.3665 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4664 5.0084 0.6711 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0557 7.3050 -0.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4449 6.3029 -3.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6027 1.7736 1.5655 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1803 -3.8729 -3.1024 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1183 -3.8430 -4.9312 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7385 -2.4525 -4.0324 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 3 14 15 1 0 14 16 1 0 11 17 1 0 10 18 1 0 7 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 23 27 1 0 27 28 2 0 23 29 1 1 29 30 1 0 30 31 2 3 31 32 1 0 31 33 1 0 20 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 40 42 1 0 39 43 1 0 19 44 1 0 2 45 1 0 24 5 1 0 41 36 1 0 27 7 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 6 6 53 1 0 6 54 1 0 8 55 1 0 8 56 1 0 9 57 1 0 11 58 1 6 12 59 1 0 12 60 1 0 13 61 1 0 15 62 1 0 15 63 1 0 15 64 1 0 16 65 1 0 16 66 1 0 16 67 1 0 17 68 1 0 18 69 1 0 18 70 1 0 18 71 1 0 25 72 1 0 25 73 1 0 25 74 1 0 26 75 1 0 26 76 1 0 26 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 32 81 1 0 32 82 1 0 32 83 1 0 33 84 1 0 33 85 1 0 33 86 1 0 37 87 1 0 38 88 1 0 41 89 1 0 42 90 1 0 43 91 1 0 44 92 1 0 45 93 1 0 45 94 1 0 45 95 1 0 M END

Standard InCHIKey	ONKOOMBIYOLKEL-MCDUMTBSSA-N
Standard InCHI	InChI=1S/C38H50O7/c1-22(2)10-13-27-21-37(18-17-25(7)28(39)14-11-23(3)4)33(43)31(32(42)26-12-15-29(40)30(41)20-26)34(44)38(35(37)45,36(27,8)9)19-16-24(5)6/h10-12,15-17,20,27-28,39-41,43H,13-14,18-19,21H2,1-9H3/b25-17+/t27-,28+,37+,38-/m1/s1
SMILES	CC(=CC[C@@H]1C[C@@]2(C/C=C(/[C@H](CC=C(C)C)O)C)C(=C(C(=O)[C@@](C1(C)C)(C2=O)CC=C(C)C)C(=O)c1ccc(c(c1)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	618.36	Volume:	672.665 ? Van der Waals volume.
Dense:	0.919	LogP:	5.304 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.327 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.124 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
TPSA:	132.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.065	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.669	Fsp³:	0.5
MCE-18:	101.614 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.995	Fluc inhibitor:	0.111 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.149 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.45 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.576	Promiscuous compounds:	0.238

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.875	MDCK Permeability:	-4.714
Pgp-inhibitor:	0.0	Pgp-substrate:	0.039
PAMPA:	0.998 ? 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):	0.0
20% Bioavailability (F20%):	0.02	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.947
Plasma Protein Binding (PPB):	85.38%	Volume Distribution (VD):	0.121
Fu:	18.535% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.115	BCRP inhibitor:	0.002
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.822	CYP2C19-substrate:	0.122
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.841
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.959
HLM stability:	0.996 ? 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):

6.52

Half-life (T1/2):

1.299

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.227
Human Hepatotoxicity (H-HT):	0.927	Drug-induced Liver Injury (DILI):	0.95
AMES Toxicity:	0.512	Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.913	Skin Sensitization:	0.998
Carcinogencity:	0.647	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.932
Drug-induced Neurotoxicity:	0.086	Ototoxicity:	0.983
Hematotoxicity:	0.901	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.109
A549 Cytotoxicity:	0.947	Hek293 Cytotoxicity:	0.393
BCF:	1.573 ? 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:	5.227 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.221 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.873 ? 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
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21028890]
NPO30436	Rheedia edulis	Species	Clusiaceae	Eukaryota	seeds and rinds	n.a.	n.a.	PMID[21028890]
NPO4768	Lunaria annua	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39202882]
NPO6556	Garcinia intermedia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4768	Lunaria annua	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3858	Pimpinella magna	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6556	Garcinia intermedia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO104	Hymenodictyon floribundum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4768	Lunaria annua	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3858	Pimpinella magna	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10493	Casearia thwaitesii	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1970	Rubus palmatus	Species	Rosaceae	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

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Others	1
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	45580.0	nM	PMID[21028890]
NPT1	Others	Radical scavenging activity	n.a.	IC50	=	38320.0	nM	PMID[21028890]

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 NPC30846 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	7119
0.1-0.2	41084
0.2-0.3	1535
0.3-0.4	43
0.4-0.5	25
0.5-0.6	11
0.6-0.7	20
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
0.875	High Similarity	NPC149773
0.7778	Intermediate Similarity	NPC165191
0.7778	Intermediate Similarity	NPC177501
0.7639	Intermediate Similarity	NPC114333
0.7639	Intermediate Similarity	NPC28592
0.7639	Intermediate Similarity	NPC51531
0.7606	Intermediate Similarity	NPC46242
0.7606	Intermediate Similarity	NPC91887
0.7606	Intermediate Similarity	NPC93556
0.7568	Intermediate Similarity	NPC471971
0.7568	Intermediate Similarity	NPC471972
0.7568	Intermediate Similarity	NPC469855
0.7534	Intermediate Similarity	NPC473479
0.7534	Intermediate Similarity	NPC50615
0.7534	Intermediate Similarity	NPC141650
0.75	Intermediate Similarity	NPC297797
0.7297	Intermediate Similarity	NPC469857
0.7297	Intermediate Similarity	NPC245760
0.7222	Intermediate Similarity	NPC289358
0.7222	Intermediate Similarity	NPC4289
0.7222	Intermediate Similarity	NPC42384
0.6812	Remote Similarity	NPC259400
0.6812	Remote Similarity	NPC130591
0.6812	Remote Similarity	NPC234637
0.6795	Remote Similarity	NPC469856
0.6709	Remote Similarity	NPC471970
0.6667	Remote Similarity	NPC469854
0.6667	Remote Similarity	NPC5014
0.6538	Remote Similarity	NPC482621
0.6538	Remote Similarity	NPC23667
0.6538	Remote Similarity	NPC157284
0.6538	Remote Similarity	NPC294330
0.6463	Remote Similarity	NPC482617
0.6463	Remote Similarity	NPC482616
0.625	Remote Similarity	NPC603871
0.6203	Remote Similarity	NPC479148
0.6173	Remote Similarity	NPC237441
0.6164	Remote Similarity	NPC611064
0.6154	Remote Similarity	NPC198803
0.6145	Remote Similarity	NPC482618
0.6125	Remote Similarity	NPC479151
0.5921	Remote Similarity	NPC473779
0.5595	Remote Similarity	NPC25736
0.5556	Remote Similarity	NPC48949
0.5556	Remote Similarity	NPC473527
0.5529	Remote Similarity	NPC479146
0.5476	Remote Similarity	NPC482619
0.5072	Remote Similarity	NPC602123
0.5059	Remote Similarity	NPC8493
0.5059	Remote Similarity	NPC469375
0.5059	Remote Similarity	NPC110855
0.5059	Remote Similarity	NPC144247

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC30846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3200
0.1-0.2	5888
0.2-0.3	62
0.3-0.4	0
0.4-0.5	0
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