NPASS Compound

Natural Product: NPC256207

Natural Product ID	NPC256207
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NQZFCGVSKVDIOM-DBMZJTKCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101622423
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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 74 77 0 0 0 0 0 0 0 0999 V2000 5.8884 -2.5915 0.4228 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8038 -1.6903 1.3578 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8408 -0.4672 1.0718 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5519 -1.1603 1.0281 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2107 -0.6036 0.8623 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8762 0.0862 -0.3939 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0501 -0.8167 -1.6029 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4971 0.7207 -0.3991 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3888 1.3968 -1.7681 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9977 1.0605 -2.2684 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7152 0.7165 -0.9808 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9184 1.0153 -0.6108 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7994 1.8085 -1.5178 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0833 1.8984 -1.2244 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6386 1.2387 -0.0387 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7861 1.6615 0.4987 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3117 0.9899 1.6714 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0756 1.5938 2.4565 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9027 -0.4427 1.8964 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3967 -0.4461 1.7968 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8656 0.0969 0.5166 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9076 -0.9996 -0.5491 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4457 0.5935 0.7037 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6009 -0.3849 1.4233 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1248 -0.1068 1.2267 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6950 -0.0802 -0.2017 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7843 -1.4510 -0.7653 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5220 0.1090 -0.0993 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0809 1.3605 -0.7313 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0361 0.2767 0.1837 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9361 0.3353 2.2196 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1608 0.7346 2.4187 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5577 -3.4808 0.5742 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3944 -2.6341 -0.5342 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3224 -1.7111 2.2833 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7122 -2.0108 0.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5248 -1.8973 1.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5059 -1.4794 1.0670 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9257 0.0820 1.7324 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5255 0.9479 -0.5275 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3292 -1.8322 -1.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1763 -0.8605 -2.2626 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9099 -0.5138 -2.2383 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5356 1.5397 0.3468 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4546 2.5219 -1.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2027 1.1289 -2.4326 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4294 1.9620 -2.7471 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0410 0.2543 -2.9987 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3923 2.2827 -2.3724 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7648 2.4662 -1.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3180 2.4939 0.0663 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1809 -0.7217 2.9234 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3919 -1.0302 1.1197 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9787 0.0472 2.6919 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0869 -1.5262 1.8536 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9506 -1.0207 -0.9218 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6763 -1.9807 -0.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1719 -0.7873 -1.3543 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5258 1.5119 1.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7700 -0.2200 2.5320 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8680 -1.4439 1.2686 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8813 0.8554 1.7451 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6049 -0.8975 1.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1136 -1.4083 -1.8462 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0324 -2.1356 -0.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6780 -1.9487 -0.2774 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5326 -0.7255 -0.8908 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5205 1.1645 -1.6663 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9724 1.9771 -1.1150 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5067 2.0203 -0.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2522 1.3299 0.4702 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5413 0.1404 -0.7941 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4123 -0.4814 0.8706 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1823 1.5688 2.9475 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 3 28 1 0 28 29 1 0 28 30 1 0 3 31 1 1 31 32 1 0 26 8 1 0 26 11 1 0 23 12 1 0 21 15 1 0 1 33 1 0 1 34 1 0 2 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 6 40 1 6 7 41 1 0 7 42 1 0 7 43 1 0 8 44 1 1 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 13 49 1 0 14 50 1 0 16 51 1 0 19 52 1 0 19 53 1 0 20 54 1 0 20 55 1 0 22 56 1 0 22 57 1 0 22 58 1 0 23 59 1 1 24 60 1 0 24 61 1 0 25 62 1 0 25 63 1 0 27 64 1 0 27 65 1 0 27 66 1 0 28 67 1 0 29 68 1 0 29 69 1 0 29 70 1 0 30 71 1 0 30 72 1 0 30 73 1 0 32 74 1 0 M END

Standard InCHIKey	NQZFCGVSKVDIOM-DBMZJTKCSA-N
Standard InCHI	InChI=1S/C29H42O3/c1-7-29(32-31,19(2)3)17-12-20(4)24-10-11-25-23-9-8-21-18-22(30)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,24,26,31H,1,10-17H2,2-6H3/t20-,24-,26+,27+,28-,29+/m1/s1
SMILES	C=C[C@](CC[C@@H](C)[C@H]1CCC2=C3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)(C(C)C)OO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	438.31	Volume:	489.103 ? Van der Waals volume.
Dense:	0.896	LogP:	5.87 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.286 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.881 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	22.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.255	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.119	Fsp³:	0.69
MCE-18:	69.837 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.98	Fluc inhibitor:	0.3 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.595	Promiscuous compounds:	0.176

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.127	MDCK Permeability:	-4.895
Pgp-inhibitor:	0.938	Pgp-substrate:	0.004
PAMPA:	0.009 ? 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%):	0.197	30% Bioavailability (F30%):	0.984
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056	MRP1:	0.182
Plasma Protein Binding (PPB):	97.017%	Volume Distribution (VD):	0.277
Fu:	2.832% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.81
BSEP inhibitor:	0.984

ADMET: Metabolism

CYP1A2-inhibitor:	0.015	CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.986	CYP2C19-substrate:	0.55
CYP2C9-inhibitor:	0.19	CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.017	CYP2D6-substrate:	0.997
CYP3A4-inhibitor:	0.992	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.994 ? 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):

10.307

Half-life (T1/2):

0.282

ADMET: Toxicity

hERG Blockers:	0.207	hERG Blockers (10um):	0.442
Human Hepatotoxicity (H-HT):	0.79	Drug-induced Liver Injury (DILI):	0.755
AMES Toxicity:	0.577	Rat Oral Acute Toxicity:	0.526
Maximum Recommended Daily Dose:	0.661	Skin Sensitization:	0.992
Carcinogencity:	0.563	Eye Corrosion:	0.017
Eye Irritation:	0.257	Respiratory Toxicity:	0.236
Drug-induced Neurotoxicity:	0.571	Ototoxicity:	0.433
Hematotoxicity:	0.34	Drug-induced Nephrotoxicity:	0.188
Genotoxicity:	0.95	RPMI-8226 Immunitoxicity:	0.216
A549 Cytotoxicity:	0.131	Hek293 Cytotoxicity:	0.618
BCF:	2.18 ? 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:	4.71 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.13 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.642 ? 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 NPC256207 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	21834
0.1-0.2	26915
0.2-0.3	1051
0.3-0.4	51
0.4-0.5	4
0.5-0.6	2
0.6-0.7	1
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	Natural Product ID
0.623	Remote Similarity	NPC205917
0.507	Remote Similarity	NPC607047
0.507	Remote Similarity	NPC609074

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC256207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7225
0.1-0.2	1813
0.2-0.3	98
0.3-0.4	14
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