NPASS Compound

Natural Product: NPC225240

Natural Product ID	NPC225240
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XUARCIYIVXVTAE-AZUMOFOVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6708704
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 82 86 0 0 0 0 0 0 0 0999 V2000 -4.0842 2.6914 0.3696 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5966 1.6977 -0.6540 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5652 0.7930 0.0259 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8271 -0.0800 0.9654 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6972 -0.8792 0.3628 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9355 -1.4002 1.5502 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4786 -1.6219 1.3585 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8020 -0.3548 0.8783 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1745 0.7331 1.8711 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4466 -0.0402 -0.4181 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7040 0.3920 -1.4066 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7935 0.5955 -1.3235 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2845 -0.5677 -0.5037 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7439 -0.7268 -0.5593 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0083 -2.2439 -0.7006 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2344 -0.1535 -1.8806 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7142 -0.3846 -2.0859 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4653 0.3405 -1.0384 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6313 0.8421 0.1042 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1803 2.2233 -0.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6063 0.9175 1.2998 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5633 -0.1414 0.5400 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8445 0.3527 1.7323 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3924 0.6792 1.5408 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.4979 0.8697 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0463 -1.6938 1.7172 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5501 -0.4366 -0.5871 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9063 -0.2073 -0.6960 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5290 0.9502 -1.3618 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1073 0.6188 -2.7580 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4016 -2.1324 -0.2224 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0529 -2.8412 0.7626 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3805 3.7421 0.1466 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4081 2.4233 1.3743 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9592 2.7195 0.3272 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1135 2.3291 -1.4230 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2364 1.4464 0.6526 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2472 0.2599 -0.6609 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5466 0.4741 1.8854 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5772 -0.8390 1.3496 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0564 -0.7459 2.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3508 -2.3861 1.9255 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0782 -1.8170 2.3981 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3394 -2.4757 0.6819 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2498 0.9976 1.8272 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6583 1.6922 1.6958 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0207 0.3309 2.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1922 0.6207 -2.3433 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0280 1.5824 -0.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1420 0.4188 -2.3749 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7733 -1.4642 -0.9820 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3690 -2.5300 -1.6833 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7573 -2.5794 0.0430 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0864 -2.8348 -0.5258 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7186 -0.7739 -2.6727 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0610 0.9077 -2.0110 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0206 -1.4258 -2.1094 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9319 0.0265 -3.1150 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9401 1.2438 -1.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1169 2.4297 -0.1625 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6255 2.9884 0.5488 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5615 2.5750 -1.1621 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3255 1.7230 1.9908 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6773 -0.0762 1.7916 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6339 1.1446 0.9334 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2023 -1.0052 0.9229 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9179 -0.3064 2.6330 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3271 1.3171 2.0793 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9360 0.7523 2.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2256 1.6320 1.0468 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1324 -1.9212 1.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5305 -2.6173 1.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8605 -1.4154 2.7761 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2234 -1.1157 0.0234 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8758 -0.9971 -1.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7579 1.7179 -1.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3022 1.5786 -3.2827 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3558 0.0810 -3.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0665 0.1052 -2.6764 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6018 -2.7923 -0.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1478 -1.8361 -0.9706 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0215 -2.7292 0.7150 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 1 18 27 1 0 10 28 1 0 28 29 1 0 29 30 1 0 5 31 1 6 31 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 1 35 1 0 2 36 1 6 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 9 45 1 0 9 46 1 0 9 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 15 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 6 20 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 26 71 1 0 26 72 1 0 26 73 1 0 27 74 1 0 28 75 1 6 29 76 1 6 30 77 1 0 30 78 1 0 30 79 1 0 31 80 1 0 31 81 1 0 32 82 1 0 M END

Standard InCHIKey	XUARCIYIVXVTAE-AZUMOFOVSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3/t19-,20+,22?,23?,24+,25+,27+,28-,29-,30-/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CCC4[C@@]5(C)CC[C@@H](C(C)(C)C5CC[C@@]34C)O)[C@@H]2[C@H]1C)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	4.895 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.998 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.499 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.429	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.823	Fsp³:	0.933
MCE-18:	99.517 ? 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:	0.677	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? 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:	0.353	Promiscuous compounds:	0.038

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.369	MDCK Permeability:	-5.0
Pgp-inhibitor:	0.039	Pgp-substrate:	0.526
PAMPA:	0.883 ? 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%):	0.972	30% Bioavailability (F30%):	0.433
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999	MRP1:	0.952
Plasma Protein Binding (PPB):	89.732%	Volume Distribution (VD):	-0.186
Fu:	9.576% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.166	BCRP inhibitor:	0.494
BSEP inhibitor:	0.925

ADMET: Metabolism

CYP1A2-inhibitor:	0.506	CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.352
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.953
CYP3A4-inhibitor:	0.994	CYP3A4-substrate:	0.992
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.551
HLM stability:	0.102 ? 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):

10.757

Half-life (T1/2):

0.571

ADMET: Toxicity

hERG Blockers:	0.12	hERG Blockers (10um):	0.316
Human Hepatotoxicity (H-HT):	0.716	Drug-induced Liver Injury (DILI):	0.059
AMES Toxicity:	0.212	Rat Oral Acute Toxicity:	0.385
Maximum Recommended Daily Dose:	0.714	Skin Sensitization:	0.946
Carcinogencity:	0.884	Eye Corrosion:	0.005
Eye Irritation:	0.598	Respiratory Toxicity:	0.77
Drug-induced Neurotoxicity:	0.112	Ototoxicity:	0.669
Hematotoxicity:	0.255	Drug-induced Nephrotoxicity:	0.428
Genotoxicity:	0.419	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.714	Hek293 Cytotoxicity:	0.72
BCF:	2.501 ? 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:	4.522 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.55 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.228 ? 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
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787443]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	stem	n.a.	PMID[16252920]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	calyx	n.a.	PMID[21561086]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	fruit	n.a.	PMID[24086493]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37324556]
NPO4657	Cynanchum rostellatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30717	Metaplexis japonica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30717	Metaplexis japonica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4657	Cynanchum rostellatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30717	Metaplexis japonica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18296	Diospyros kaki	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4657	Cynanchum rostellatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14547	Ilex pubescens	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	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 NPC225240 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	26617
0.1-0.2	19636
0.2-0.3	2720
0.3-0.4	684
0.4-0.5	126
0.5-0.6	55
0.6-0.7	7
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC40394
0.8113	Intermediate Similarity	NPC27765
0.8113	Intermediate Similarity	NPC122418
0.8113	Intermediate Similarity	NPC491014
0.7414	Intermediate Similarity	NPC95594
0.7167	Intermediate Similarity	NPC40552
0.7069	Intermediate Similarity	NPC132478
0.7049	Intermediate Similarity	NPC477579
0.678	Remote Similarity	NPC101475
0.6774	Remote Similarity	NPC479748
0.6667	Remote Similarity	NPC304285
0.6552	Remote Similarity	NPC120098
0.6271	Remote Similarity	NPC290598
0.6271	Remote Similarity	NPC30590
0.6129	Remote Similarity	NPC291379
0.5821	Remote Similarity	NPC51700
0.5821	Remote Similarity	NPC88716
0.5821	Remote Similarity	NPC68160
0.5714	Remote Similarity	NPC311078
0.5714	Remote Similarity	NPC196753
0.5672	Remote Similarity	NPC610937
0.5625	Remote Similarity	NPC235341
0.5625	Remote Similarity	NPC253807
0.5625	Remote Similarity	NPC158662
0.5588	Remote Similarity	NPC307335
0.5588	Remote Similarity	NPC74855
0.5588	Remote Similarity	NPC195019
0.5538	Remote Similarity	NPC159168
0.5538	Remote Similarity	NPC602872
0.5507	Remote Similarity	NPC18872
0.5507	Remote Similarity	NPC290614
0.5441	Remote Similarity	NPC274330
0.5373	Remote Similarity	NPC246708
0.5362	Remote Similarity	NPC182797
0.5362	Remote Similarity	NPC171203
0.5362	Remote Similarity	NPC307426
0.5362	Remote Similarity	NPC98442
0.5362	Remote Similarity	NPC242468
0.5362	Remote Similarity	NPC52169
0.5362	Remote Similarity	NPC488562
0.5231	Remote Similarity	NPC237344
0.5231	Remote Similarity	NPC34177
0.5217	Remote Similarity	NPC480946
0.5217	Remote Similarity	NPC187722
0.5217	Remote Similarity	NPC130577
0.5217	Remote Similarity	NPC142415
0.5217	Remote Similarity	NPC102683
0.5217	Remote Similarity	NPC86372
0.5211	Remote Similarity	NPC49776
0.5211	Remote Similarity	NPC63118
0.5211	Remote Similarity	NPC474436
0.5181	Remote Similarity	NPC477292
0.5156	Remote Similarity	NPC82477
0.5152	Remote Similarity	NPC290495
0.5152	Remote Similarity	NPC480924
0.5143	Remote Similarity	NPC7260
0.5143	Remote Similarity	NPC210037
0.5143	Remote Similarity	NPC120968
0.5143	Remote Similarity	NPC227467
0.5143	Remote Similarity	NPC273621
0.5143	Remote Similarity	NPC112866
0.5075	Remote Similarity	NPC230295
0.5075	Remote Similarity	NPC238992
0.5075	Remote Similarity	NPC470588
0.5075	Remote Similarity	NPC98386
0.5072	Remote Similarity	NPC477872
0.507	Remote Similarity	NPC61543
0.507	Remote Similarity	NPC293048
0.507	Remote Similarity	NPC225585
0.506	Remote Similarity	NPC182249

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC225240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8027
0.1-0.2	1086
0.2-0.3	33
0.3-0.4	3
0.4-0.5	0
0.5-0.6	1
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
0.5143	Remote Similarity	NPD7645	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