NPASS Compound

Natural Product: NPC282439

Natural Product ID	NPC282439
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QGJZLNKBHJESQX-ITHVIPIZSA-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:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 81 85 0 0 0 0 0 0 0 0999 V2000 -5.8467 -1.8696 0.9604 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5474 -1.7135 1.0556 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7301 -2.9784 1.1991 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8698 -0.3942 1.0403 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8719 0.6829 1.0036 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0252 0.9500 -0.4679 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6634 0.6404 -1.0732 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0040 1.9493 -1.3537 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5115 1.7398 -1.6293 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9046 1.3223 -0.2991 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2518 2.4182 0.6551 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5211 0.0235 0.1396 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0593 -0.1424 1.5960 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4560 -0.4038 1.5394 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2080 0.6935 0.8444 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6601 0.3295 0.8008 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5189 1.5471 1.1995 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9209 -0.6876 1.9149 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3537 -1.1931 1.8902 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4766 -1.9621 0.6041 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3159 -1.0373 -0.5420 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 -1.9234 -1.8005 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6233 -0.2345 -0.6534 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1649 -0.1186 -0.5272 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0530 -0.6841 -1.4172 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9778 0.3457 -1.6414 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6210 1.1564 -0.4425 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0808 2.5953 -0.7476 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7867 -2.4876 0.5644 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9200 -0.2458 -0.1225 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9464 0.0072 -2.3931 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5654 -1.1426 -2.6680 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6577 0.7632 -3.3049 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2765 -2.8937 0.9895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5956 -1.1108 0.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8791 -3.3193 2.2308 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1871 -3.7273 0.5195 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6946 -2.8306 0.8941 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3599 -0.3101 2.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4530 1.5920 1.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8430 0.5021 1.4761 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2963 2.0210 -0.5808 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8334 0.3554 -0.8828 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2027 2.6625 -0.5607 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4058 2.3894 -2.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1602 2.7312 -1.9585 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4615 0.9868 -2.4111 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5383 2.6505 1.4358 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4341 3.4029 0.1258 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2080 2.2087 1.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8703 -0.7476 -0.3919 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2830 0.7334 2.2027 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4522 -1.0924 2.0302 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7699 -0.4885 2.5831 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5077 -1.3774 0.9672 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1496 1.5691 1.5620 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 2.3383 1.5974 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1418 1.8999 0.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1895 1.3451 2.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3130 -1.5890 1.8422 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7887 -0.1286 2.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4036 -1.9360 2.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1172 -0.4580 2.0736 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7809 -2.8100 0.6138 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5206 -1.3517 -2.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2264 -2.5833 -1.6545 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4683 -2.6033 -1.8287 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3512 0.6348 -1.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9933 0.0914 0.3164 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4007 -0.8145 -1.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4913 0.8068 -1.0969 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5646 -0.8743 -2.4088 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6979 -1.6594 -1.0880 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3105 0.9807 -2.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1165 -0.2363 -2.0843 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8677 2.7609 -1.8478 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1551 2.7357 -0.6628 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5856 3.3317 -0.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0568 -2.8257 1.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9822 -1.2710 -0.6196 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0070 0.3629 -4.1721 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 20 29 1 0 12 30 1 0 7 31 1 6 31 32 2 0 31 33 1 0 30 4 1 0 30 7 1 0 27 10 1 0 27 15 1 0 24 16 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 1 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 11 48 1 0 11 49 1 0 11 50 1 0 12 51 1 6 13 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 15 56 1 1 17 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 20 64 1 1 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 23 70 1 0 24 71 1 6 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 28 76 1 0 28 77 1 0 28 78 1 0 29 79 1 0 30 80 1 6 33 81 1 0 M END

Standard InCHIKey	QGJZLNKBHJESQX-ITHVIPIZSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20-,21+,22-,23-,24+,27-,28-,29+,30+/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@]2(CC[C@@]3(C)[C@@H](CC[C@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@H]5CC[C@@]34C)O)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	505.751 ? Van der Waals volume.
Dense:	0.902	LogP:	3.91 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.655 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.306 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
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:	0.436	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.689	Fsp³:	0.9
MCE-18:	104.0 ? 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:	0.843	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.378	Promiscuous compounds:	0.146

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.354	MDCK Permeability:	-4.877
Pgp-inhibitor:	0.0	Pgp-substrate:	0.018
PAMPA:	0.999 ? 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%):	0.106	30% Bioavailability (F30%):	0.025
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.347
Plasma Protein Binding (PPB):	90.911%	Volume Distribution (VD):	-0.108
Fu:	10.944% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	0.891	BCRP inhibitor:	0.159
BSEP inhibitor:	0.065

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.884	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.016	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.138	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.026
HLM stability:	0.008 ? 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):

7.139

Half-life (T1/2):

0.918

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.043
Human Hepatotoxicity (H-HT):	0.603	Drug-induced Liver Injury (DILI):	0.381
AMES Toxicity:	0.288	Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.362	Skin Sensitization:	0.949
Carcinogencity:	0.908	Eye Corrosion:	0.286
Eye Irritation:	0.922	Respiratory Toxicity:	0.912
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.645
Hematotoxicity:	0.589	Drug-induced Nephrotoxicity:	0.915
Genotoxicity:	0.061	RPMI-8226 Immunitoxicity:	0.015
A549 Cytotoxicity:	0.153	Hek293 Cytotoxicity:	0.115
BCF:	2.101 ? 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:	4.783 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.071 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.555 ? 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
NPO15262	Dunaliella tertiolecta	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26811	Gynostemma yixingense	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2606	Hypnum cupressiforme	Species	Hypnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2762	Senna lindheimeriana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6497	Patiria miniata	Species	Asterinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4620	Marasmius prasiosmus	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO921	Helichrysum subulifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5544	Endiandra xanthocarpa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9	Camarops microspora	Species	Boliniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26811	Gynostemma yixingense	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26811	Gynostemma yixingense	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5003	Amelanchier spicata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15262	Dunaliella tertiolecta	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2606	Hypnum cupressiforme	Species	Hypnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9	Camarops microspora	Species	Boliniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26811	Gynostemma yixingense	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14867	Acer griseum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12995	Adenia cissampeloides	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4620	Marasmius prasiosmus	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8769	Mythimna loreyi	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6497	Patiria miniata	Species	Asterinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5544	Endiandra xanthocarpa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2762	Senna lindheimeriana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO921	Helichrysum subulifolium	Species	Asteraceae	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 NPC282439 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	21858
0.1-0.2	23190
0.2-0.3	3835
0.3-0.4	683
0.4-0.5	163
0.5-0.6	72
0.6-0.7	25
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC264317
1.0	High Similarity	NPC294438
0.8772	High Similarity	NPC16377
0.8448	Intermediate Similarity	NPC151191
0.8421	Intermediate Similarity	NPC488164
0.8421	Intermediate Similarity	NPC264005
0.7833	Intermediate Similarity	NPC2783
0.7627	Intermediate Similarity	NPC30583
0.75	Intermediate Similarity	NPC488506
0.75	Intermediate Similarity	NPC220498
0.7302	Intermediate Similarity	NPC488165
0.7213	Intermediate Similarity	NPC476071
0.7213	Intermediate Similarity	NPC213832
0.7097	Intermediate Similarity	NPC201655
0.7	Intermediate Similarity	NPC472608
0.6984	Remote Similarity	NPC18064
0.6949	Remote Similarity	NPC68828
0.6774	Remote Similarity	NPC80590
0.6667	Remote Similarity	NPC24772
0.6667	Remote Similarity	NPC211162
0.6667	Remote Similarity	NPC183374
0.6667	Remote Similarity	NPC291373
0.6667	Remote Similarity	NPC30322
0.6615	Remote Similarity	NPC269360
0.6615	Remote Similarity	NPC475061
0.6613	Remote Similarity	NPC192744
0.6562	Remote Similarity	NPC271974
0.6562	Remote Similarity	NPC247312
0.6515	Remote Similarity	NPC486704
0.6462	Remote Similarity	NPC4309
0.6418	Remote Similarity	NPC169933
0.6393	Remote Similarity	NPC246445
0.6364	Remote Similarity	NPC488213
0.6308	Remote Similarity	NPC195395
0.6269	Remote Similarity	NPC160506
0.6216	Remote Similarity	NPC486709
0.6176	Remote Similarity	NPC478841
0.6176	Remote Similarity	NPC488166
0.6119	Remote Similarity	NPC601275
0.6061	Remote Similarity	NPC277399
0.5974	Remote Similarity	NPC486699
0.5942	Remote Similarity	NPC600004
0.5909	Remote Similarity	NPC474686
0.5882	Remote Similarity	NPC474719
0.5846	Remote Similarity	NPC119743
0.5833	Remote Similarity	NPC192638
0.5833	Remote Similarity	NPC25511
0.5833	Remote Similarity	NPC600137
0.5823	Remote Similarity	NPC290349
0.5797	Remote Similarity	NPC611139
0.5775	Remote Similarity	NPC481311
0.5735	Remote Similarity	NPC57954
0.5714	Remote Similarity	NPC601176
0.5714	Remote Similarity	NPC608379
0.5672	Remote Similarity	NPC181225
0.56	Remote Similarity	NPC606354
0.5588	Remote Similarity	NPC474512
0.5556	Remote Similarity	NPC231256
0.5556	Remote Similarity	NPC178383
0.5538	Remote Similarity	NPC298168
0.5538	Remote Similarity	NPC143133
0.5493	Remote Similarity	NPC607677
0.5476	Remote Similarity	NPC51947
0.5476	Remote Similarity	NPC486700
0.5476	Remote Similarity	NPC275312
0.5469	Remote Similarity	NPC93662
0.5467	Remote Similarity	NPC602512
0.5455	Remote Similarity	NPC12774
0.5397	Remote Similarity	NPC104387
0.5385	Remote Similarity	NPC246956
0.5385	Remote Similarity	NPC74595
0.5385	Remote Similarity	NPC264665
0.5385	Remote Similarity	NPC269396
0.5352	Remote Similarity	NPC252714
0.5349	Remote Similarity	NPC487491
0.5325	Remote Similarity	NPC605397
0.5323	Remote Similarity	NPC212733
0.5312	Remote Similarity	NPC42853
0.5312	Remote Similarity	NPC248830
0.5312	Remote Similarity	NPC212241
0.5286	Remote Similarity	NPC274330
0.5278	Remote Similarity	NPC293564
0.5254	Remote Similarity	NPC232112
0.5238	Remote Similarity	NPC475138
0.5238	Remote Similarity	NPC185536
0.5224	Remote Similarity	NPC49599
0.5224	Remote Similarity	NPC49627
0.5211	Remote Similarity	NPC51700
0.5211	Remote Similarity	NPC88716
0.5211	Remote Similarity	NPC68160
0.5205	Remote Similarity	NPC19530
0.5156	Remote Similarity	NPC91573
0.5152	Remote Similarity	NPC119355
0.5147	Remote Similarity	NPC471900
0.5135	Remote Similarity	NPC603461
0.5128	Remote Similarity	NPC611262
0.5119	Remote Similarity	NPC248287
0.5119	Remote Similarity	NPC234548
0.5079	Remote Similarity	NPC606606
0.5077	Remote Similarity	NPC237460
0.507	Remote Similarity	NPC480946
0.507	Remote Similarity	NPC187722
0.507	Remote Similarity	NPC130577
0.507	Remote Similarity	NPC142415
0.507	Remote Similarity	NPC102683
0.507	Remote Similarity	NPC198664
0.5068	Remote Similarity	NPC202728
0.5068	Remote Similarity	NPC158059
0.5068	Remote Similarity	NPC480563
0.5068	Remote Similarity	NPC606728
0.5057	Remote Similarity	NPC101863
0.5056	Remote Similarity	NPC488205

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC282439 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5881
0.1-0.2	3161
0.2-0.3	95
0.3-0.4	9
0.4-0.5	1
0.5-0.6	1
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	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7520	Phase 1
0.6269	Remote Similarity	NPD8035	Phase 2
0.5422	Remote Similarity	NPD8034	Phase 2

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