NPASS Compound

Natural Product: NPC217210

Natural Product ID	NPC217210
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OILXMJHPFNGGTO-HMDLNFLYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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 75 78 0 0 0 0 0 0 0 0999 V2000 6.8676 0.5605 0.4087 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5017 -0.6288 -0.4553 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4375 -0.2387 -1.9270 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3181 -1.3715 0.0051 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5922 -1.8773 1.4059 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0144 -0.7027 -0.0012 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7759 0.5450 -0.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4665 1.2445 -0.3267 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6441 2.6121 0.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3170 0.4805 0.1386 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2779 0.0170 1.5585 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0537 -0.9170 1.4507 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9118 -0.0232 0.6867 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6549 -0.9148 -0.2868 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1967 -2.0901 0.4359 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5108 -1.7823 1.0340 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3199 -0.8781 0.5233 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6239 -0.6442 1.1999 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6845 -0.9671 0.1657 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1425 -1.3568 -1.1669 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0613 -0.4927 -1.7193 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0177 -0.0861 -0.6888 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3445 1.3801 -0.3692 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6160 -0.1970 -1.1638 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0024 1.1511 -1.5066 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4763 1.0522 -1.5096 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0525 1.0213 -0.0404 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3360 2.3484 0.5759 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6822 -0.0124 0.0842 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1487 0.7006 1.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8581 0.4105 0.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0194 1.4907 -0.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3667 -1.3299 -0.3896 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4554 -0.6023 -2.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5824 0.8465 -2.0783 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2082 -0.7546 -2.5324 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2202 -2.2853 -0.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6376 -2.2330 1.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4408 -1.0803 2.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9087 -2.7520 1.5664 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1774 -1.3398 0.2599 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7007 1.0853 -0.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2908 1.4905 -1.4224 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6904 2.5954 1.4038 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9965 3.3855 -0.1347 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6870 2.9272 -0.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3132 -0.4957 -0.4710 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1379 -0.4260 2.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 0.8307 2.2453 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3126 -1.1219 2.4508 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4130 -1.7774 0.8650 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6033 0.4648 1.3790 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8291 -1.3304 -0.9622 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3843 -2.9049 -0.3279 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4593 -2.4367 1.1917 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7812 -2.3494 1.9324 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7505 0.4124 1.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7236 -1.2607 2.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2018 -1.8937 0.5683 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0089 -1.2810 -1.8897 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8862 -2.4387 -1.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4725 0.3732 -2.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5081 -1.1048 -2.4902 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1535 2.0162 -1.2650 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7931 1.7156 0.5301 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4227 1.4805 -0.1552 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6519 -0.7538 -2.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3275 1.5083 -2.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2314 1.9312 -0.7562 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1166 2.0417 -1.8936 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1048 0.2016 -2.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3694 2.3228 1.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3686 3.1895 -0.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3202 2.6494 1.4010 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6334 0.6504 0.8096 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 19 29 1 0 27 10 1 0 27 13 1 0 24 14 1 0 22 17 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 4 37 1 6 5 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 7 42 1 0 8 43 1 6 9 44 1 0 9 45 1 0 9 46 1 0 10 47 1 6 11 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 1 14 53 1 6 15 54 1 0 15 55 1 0 16 56 1 0 18 57 1 0 18 58 1 0 19 59 1 1 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 6 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 M END

Standard InCHIKey	OILXMJHPFNGGTO-HMDLNFLYSA-N
Standard InCHI	InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20-,22-,23+,24+,25+,26-,27-,28+/m0/s1
SMILES	CC(C)[C@@H](C)/C=C/[C@H](C)[C@H]1CC[C@@H]2[C@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	398.35	Volume:	462.136 ? Van der Waals volume.
Dense:	0.862	LogP:	6.706 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.865 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.255 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	21.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.489	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.483	Fsp³:	0.857
MCE-18:	69.577 ? 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:	0.985	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.6	Promiscuous compounds:	0.026

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.198	MDCK Permeability:	-4.881
Pgp-inhibitor:	0.976	Pgp-substrate:	0.001
PAMPA:	0.006 ? 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%):	0.822	30% Bioavailability (F30%):	0.888
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.088
Plasma Protein Binding (PPB):	98.215%	Volume Distribution (VD):	-0.101
Fu:	1.563% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.669
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.973	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.916 ? 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):

14.879

Half-life (T1/2):

0.688

ADMET: Toxicity

hERG Blockers:	0.127	hERG Blockers (10um):	0.398
Human Hepatotoxicity (H-HT):	0.597	Drug-induced Liver Injury (DILI):	0.178
AMES Toxicity:	0.047	Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.507	Skin Sensitization:	0.932
Carcinogencity:	0.783	Eye Corrosion:	0.289
Eye Irritation:	0.901	Respiratory Toxicity:	0.597
Drug-induced Neurotoxicity:	0.068	Ototoxicity:	0.65
Hematotoxicity:	0.274	Drug-induced Nephrotoxicity:	0.462
Genotoxicity:	0.01	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.318	Hek293 Cytotoxicity:	0.542
BCF:	3.039 ? 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:	4.501 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.165 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.231 ? 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
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10075800]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10650102]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	Mandapam Coast, Tamilnadu, India	n.a.	PMID[22704923]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9463111]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16684	Alibertia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13321	Viguiera cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16684	Alibertia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13321	Viguiera cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	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 NPC217210 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	23035
0.1-0.2	22938
0.2-0.3	3456
0.3-0.4	272
0.4-0.5	82
0.5-0.6	27
0.6-0.7	28
0.7-0.8	3
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.913	High Similarity	NPC154330
0.8936	High Similarity	NPC113733
0.7917	Intermediate Similarity	NPC162742
0.7917	Intermediate Similarity	NPC304309
0.7917	Intermediate Similarity	NPC470228
0.7692	Intermediate Similarity	NPC33913
0.7451	Intermediate Similarity	NPC230301
0.74	Intermediate Similarity	NPC22105
0.74	Intermediate Similarity	NPC34019
0.74	Intermediate Similarity	NPC107059
0.74	Intermediate Similarity	NPC600590
0.7255	Intermediate Similarity	NPC136188
0.7255	Intermediate Similarity	NPC28657
0.7255	Intermediate Similarity	NPC474216
0.7115	Intermediate Similarity	NPC198968
0.7115	Intermediate Similarity	NPC285893
0.7115	Intermediate Similarity	NPC134847
0.7059	Intermediate Similarity	NPC221758
0.6981	Remote Similarity	NPC241290
0.6981	Remote Similarity	NPC164840
0.6981	Remote Similarity	NPC484739
0.6981	Remote Similarity	NPC209944
0.6981	Remote Similarity	NPC264245
0.6981	Remote Similarity	NPC155986
0.6852	Remote Similarity	NPC328714
0.6852	Remote Similarity	NPC321381
0.6727	Remote Similarity	NPC472265
0.6727	Remote Similarity	NPC318495
0.6727	Remote Similarity	NPC59453
0.6667	Remote Similarity	NPC51014
0.6607	Remote Similarity	NPC603646
0.6491	Remote Similarity	NPC243985
0.6491	Remote Similarity	NPC473943
0.6491	Remote Similarity	NPC280710
0.6491	Remote Similarity	NPC240650
0.6491	Remote Similarity	NPC155011
0.64	Remote Similarity	NPC96319
0.6379	Remote Similarity	NPC474164
0.6379	Remote Similarity	NPC47761
0.6379	Remote Similarity	NPC488870
0.6296	Remote Similarity	NPC328313
0.6071	Remote Similarity	NPC234193
0.6066	Remote Similarity	NPC601043
0.6066	Remote Similarity	NPC605412
0.6034	Remote Similarity	NPC58063
0.6034	Remote Similarity	NPC477522
0.5893	Remote Similarity	NPC76879
0.5862	Remote Similarity	NPC1272
0.5862	Remote Similarity	NPC470614
0.5818	Remote Similarity	NPC151519
0.5818	Remote Similarity	NPC307965
0.5818	Remote Similarity	NPC18603
0.5818	Remote Similarity	NPC491013
0.5714	Remote Similarity	NPC20688
0.5645	Remote Similarity	NPC474189
0.5424	Remote Similarity	NPC87604
0.5397	Remote Similarity	NPC474349
0.5312	Remote Similarity	NPC176012
0.5231	Remote Similarity	NPC5985
0.5224	Remote Similarity	NPC235126
0.5224	Remote Similarity	NPC309493
0.5224	Remote Similarity	NPC242419
0.5217	Remote Similarity	NPC158088
0.5156	Remote Similarity	NPC474970
0.5152	Remote Similarity	NPC91604
0.5147	Remote Similarity	NPC147835
0.5147	Remote Similarity	NPC253645
0.5147	Remote Similarity	NPC85001
0.5147	Remote Similarity	NPC95920
0.5143	Remote Similarity	NPC3715
0.5088	Remote Similarity	NPC81306
0.5082	Remote Similarity	NPC474207
0.5072	Remote Similarity	NPC486119

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC217210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7615
0.1-0.2	1335
0.2-0.3	169
0.3-0.4	19
0.4-0.5	7
0.5-0.6	1
0.6-0.7	1
0.7-0.8	3
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
0.7451	Intermediate Similarity	NPD7339	Approved
0.7255	Intermediate Similarity	NPD6942	Phase 4
0.7059	Intermediate Similarity	NPD4786	Phase 1
0.64	Remote Similarity	NPD3701	Pre-clinical
0.5818	Remote Similarity	NPD3667	Phase 4

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