NPASS Compound

Natural Product: NPC181165

Natural Product ID	NPC181165
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZHYCSYOPFIUANO-LTPKDCRKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101622120
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003788] Aconitane-type diterpenoid alkaloids

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 79 0 0 0 0 0 0 0 0999 V2000 -2.3176 0.9383 4.1018 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1987 1.0836 3.0759 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5998 0.3940 1.8911 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6993 1.0049 1.1979 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9642 0.2460 -0.0845 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5894 -1.0608 0.3182 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6541 -1.9747 1.0293 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4105 -2.0888 0.1724 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7380 -0.8067 -0.0939 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5601 -1.0655 -0.7966 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5745 -1.7525 0.0676 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8879 -1.0570 -0.0765 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1728 0.0408 0.8722 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2892 1.2241 0.7959 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2992 1.2793 -0.2844 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0990 1.3884 0.3121 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0322 1.4535 -0.8792 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6770 0.0823 -0.8856 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4722 0.0992 1.0667 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2946 0.1422 -1.2653 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7186 -0.4116 -1.4600 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6579 0.6137 -1.6500 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4582 0.5733 -2.7843 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3230 -0.3685 -3.6041 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4536 1.6646 -2.9772 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4383 2.4535 -1.0665 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5039 0.4546 0.6215 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3482 0.1875 1.6757 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6669 -3.1186 0.6726 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7045 -4.2511 -0.1807 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0042 0.9733 -0.9142 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2274 0.2413 -2.0986 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1867 0.8991 -2.8881 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7621 -0.0857 3.9497 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9323 1.0594 5.1321 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1020 1.6480 3.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2315 0.6892 3.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1236 2.1760 2.8416 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6132 0.8266 1.8402 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6254 2.0869 1.0851 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4372 -0.8278 0.9757 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9222 -1.5650 -0.6128 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1272 -3.0035 0.9842 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4755 -1.7893 2.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8281 -2.4457 -0.8245 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3142 -1.6734 -1.7028 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2874 -1.9019 1.1020 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7390 -2.7851 -0.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7385 -1.7687 -0.0832 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2099 -0.4069 1.9092 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9098 2.1701 0.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7906 1.3345 1.8075 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2105 2.2735 0.9587 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7786 2.2850 -0.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5222 1.6948 -1.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8935 -0.3043 -1.8812 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3624 -0.1845 1.7112 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9991 0.4490 -2.3016 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7016 -1.1618 -2.2460 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0843 2.4346 -3.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7243 2.0593 -1.9737 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3899 1.1623 -3.3446 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7138 3.1685 -0.4469 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3607 0.5319 1.4180 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0247 0.6375 2.6265 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4209 -0.9324 1.7578 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2941 -3.9416 -1.1712 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7382 -4.6499 -0.2838 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0284 -5.0416 0.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9519 0.9892 -0.3168 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7218 2.0019 -1.1848 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1498 0.9980 -2.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7294 1.9146 -3.0763 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3113 0.3961 -3.8501 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 9 8 1 1 9 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 1 0 17 18 1 0 16 19 1 0 15 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 15 26 1 6 13 27 1 0 27 28 1 0 8 29 1 0 29 30 1 0 5 31 1 6 31 32 1 0 32 33 1 0 19 3 1 0 18 5 1 0 18 9 1 0 19 9 1 0 20 10 1 0 21 12 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 0 2 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 8 45 1 6 10 46 1 6 11 47 1 0 11 48 1 0 12 49 1 6 13 50 1 1 14 51 1 0 14 52 1 0 16 53 1 1 17 54 1 0 17 55 1 0 18 56 1 6 19 57 1 1 20 58 1 6 21 59 1 6 25 60 1 0 25 61 1 0 25 62 1 0 26 63 1 0 28 64 1 0 28 65 1 0 28 66 1 0 30 67 1 0 30 68 1 0 30 69 1 0 31 70 1 0 31 71 1 0 33 72 1 0 33 73 1 0 33 74 1 0 M END

Standard InCHIKey	ZHYCSYOPFIUANO-LTPKDCRKSA-N
Standard InCHI	InChI=1S/C26H41NO6/c1-6-27-12-24(13-30-3)8-7-20(32-5)26-16-9-15-18(31-4)11-25(29,17(23(26)27)10-19(24)26)21(16)22(15)33-14(2)28/h15-23,29H,6-13H2,1-5H3/t15-,16-,17+,18+,19-,20+,21-,22+,23-,24+,25+,26-/m1/s1
SMILES	CCN1C[C@@]2(CC[C@@H]([C@@]34[C@@H]5C[C@@H]6[C@H](C[C@]([C@@H](C[C@H]23)[C@@H]14)([C@H]5[C@H]6OC(=O)C)O)OC)OC)COC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	463.29	Volume:	468.015 ? Van der Waals volume.
Dense:	0.99	LogP:	1.538 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.89 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.113 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	25.0
TPSA:	77.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.605	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.013	Fsp³:	0.962
MCE-18:	140.824 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.252	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? 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:	0.005	Promiscuous compounds:	0.688

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.189	MDCK Permeability:	-4.997
Pgp-inhibitor:	0.004	Pgp-substrate:	0.839
PAMPA:	0.508 ? 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):	0.016
20% Bioavailability (F20%):	0.4	30% Bioavailability (F30%):	0.359
50% Bioavailability (F50%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.528	MRP1:	0.974
Plasma Protein Binding (PPB):	34.764%	Volume Distribution (VD):	-0.085
Fu:	65.431% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.854
OATP1B3 inhibitor:	0.861	BCRP inhibitor:	0.02
BSEP inhibitor:	0.213

ADMET: Metabolism

CYP1A2-inhibitor:	0.192	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.956	CYP2C19-substrate:	0.012
CYP2C9-inhibitor:	0.097	CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.25	CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.205	CYP3A4-substrate:	0.759
CYP2B6-substrate:	0.92	CYP2C8-inhibitor:	0.12
HLM stability:	0.681 ? 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):

9.746

Half-life (T1/2):

1.573

ADMET: Toxicity

hERG Blockers:	0.157	hERG Blockers (10um):	0.387
Human Hepatotoxicity (H-HT):	0.432	Drug-induced Liver Injury (DILI):	0.088
AMES Toxicity:	0.743	Rat Oral Acute Toxicity:	0.562
Maximum Recommended Daily Dose:	0.499	Skin Sensitization:	0.979
Carcinogencity:	0.525	Eye Corrosion:	0.033
Eye Irritation:	0.31	Respiratory Toxicity:	0.892
Drug-induced Neurotoxicity:	0.509	Ototoxicity:	0.495
Hematotoxicity:	0.772	Drug-induced Nephrotoxicity:	0.629
Genotoxicity:	0.484	RPMI-8226 Immunitoxicity:	0.117
A549 Cytotoxicity:	0.289	Hek293 Cytotoxicity:	0.356
BCF:	0.858 ? 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:	3.489 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.968 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.365 ? 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
NPO1719	Coussarea macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880304]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18468908]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19101157]
NPO22171	Daphniphyllum oldhami	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19441852]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19618920]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719247]
NPO17478	Radermachera boniana	Species	Bignoniaceae	Eukaryota	n.a.	twig	n.a.	PMID[21469696]
NPO17478	Radermachera boniana	Species	Bignoniaceae	Eukaryota	leaves and twigs	Cuc Phuong National Park (20o 17.901 N, 105o 39.310 E), Ninh Binh, Vietnam	2007-APR	PMID[21469696]
NPO17478	Radermachera boniana	Species	Bignoniaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21469696]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	Mediterranean sponge Psammocinia sp.	coast of Israel	n.a.	PMID[21676619]
NPO21717	Acremonium chrysogenum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[23089729]
NPO14583	Elsholtzia stauntonii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1719	Coussarea macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22171	Daphniphyllum oldhami	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22747	Lycoris sanguinea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22747	Lycoris sanguinea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27182	Chrysolaena flexuosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8496	Aristolochia chamissonis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22747	Lycoris sanguinea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22747	Lycoris sanguinea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8496	Aristolochia chamissonis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1719	Coussarea macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22171	Daphniphyllum oldhami	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21717	Acremonium chrysogenum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17478	Radermachera boniana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27182	Chrysolaena flexuosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14583	Elsholtzia stauntonii	Species	Lamiaceae	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 NPC181165 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	19855
0.1-0.2	28417
0.2-0.3	1518
0.3-0.4	34
0.4-0.5	22
0.5-0.6	8
0.6-0.7	4
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
0.6528	Remote Similarity	NPC48127
0.6447	Remote Similarity	NPC476501
0.6061	Remote Similarity	NPC609143
0.6	Remote Similarity	NPC610425
0.55	Remote Similarity	NPC600720
0.5392	Remote Similarity	NPC599985
0.5392	Remote Similarity	NPC602545
0.5392	Remote Similarity	NPC610006
0.534	Remote Similarity	NPC603869
0.5288	Remote Similarity	NPC605697
0.5238	Remote Similarity	NPC603798
0.5059	Remote Similarity	NPC476497

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC181165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6041
0.1-0.2	3087
0.2-0.3	21
0.3-0.4	1
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