NPASS Compound

Natural Product: NPC86728

Natural Product ID	NPC86728
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OWODMVTTWPVWQA-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	317501
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 83 87 0 0 0 0 0 0 0 0999 V2000 6.2150 1.0828 0.7597 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3488 -0.1095 1.1174 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4802 -1.1014 0.0016 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9143 -0.6053 -1.2849 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5679 0.1036 -1.1243 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6649 -0.4591 -2.2134 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3939 -1.0332 -1.6428 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6739 -0.0254 -0.7553 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3611 1.1768 -1.5566 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6405 0.2158 0.3759 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1037 0.8105 1.4287 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3346 1.1580 1.3707 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1838 -0.0217 0.9336 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6391 0.3310 0.8625 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8710 1.8514 0.9920 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3668 -0.2440 2.0776 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6927 -0.8126 1.8254 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5296 -0.1023 0.8106 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7865 0.1038 -0.4560 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3085 -0.9765 -1.4278 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2833 1.4050 -1.1066 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6103 1.6457 -2.3077 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 -0.0140 -0.4267 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8061 -1.3789 -0.8363 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4012 -1.0751 -1.3660 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5686 -0.7353 -0.1884 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0016 -2.1019 0.2731 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6883 -0.8996 0.6317 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4191 -0.7935 3.0375 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0447 -0.2028 0.2442 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9267 0.3670 1.3018 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8223 1.5333 -1.3826 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6149 2.4702 -0.6036 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3554 1.8279 -2.6542 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9157 -0.7142 2.3501 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3166 -1.9048 2.3522 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0034 0.0464 3.5140 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1877 1.0456 1.3155 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7331 2.0329 1.0946 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4927 1.0996 -0.3130 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0767 -2.1113 0.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5717 -1.2712 -0.1573 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8059 -1.5125 -1.9491 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6439 0.0373 -1.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5088 0.3090 -2.9668 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1537 -1.3189 -2.7598 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7597 -1.3549 -2.4712 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7344 -1.9024 -1.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6352 1.0371 -2.6452 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9750 2.0492 -1.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7034 1.4860 -1.5903 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7428 1.0171 2.2875 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4196 2.0356 0.7155 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5946 1.4198 2.4455 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0684 -0.6955 1.8484 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8815 2.0359 1.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1811 2.3427 1.6685 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8025 2.3372 0.0054 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4340 0.4960 2.9087 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7071 -1.0622 2.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6839 -1.9025 1.5302 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9437 0.8496 1.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4132 -0.7398 -1.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2566 -1.9740 -0.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9207 -0.8419 -2.4358 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3569 1.2239 -1.4150 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3112 2.2506 -0.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2837 2.5970 -2.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9459 0.7645 -1.1675 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3374 -1.8486 -1.6550 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6413 -2.0398 0.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4658 -0.3058 -2.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0861 -2.0121 -1.8839 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0017 -2.8434 -0.5202 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9082 -1.9851 0.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7840 -2.4566 1.0103 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4250 -0.3950 0.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9471 -1.3985 3.6869 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1522 -1.3299 0.3455 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8791 1.4506 1.4408 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6050 -0.0947 2.2892 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7006 2.7743 -2.8072 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7711 -0.1130 4.1688 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 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 18 28 1 0 17 29 1 0 10 30 1 0 30 31 1 0 5 32 1 0 32 33 2 0 32 34 1 0 2 35 1 0 35 36 2 0 35 37 1 0 31 2 1 0 30 5 1 0 26 8 1 0 26 13 1 0 23 14 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 6 45 1 0 6 46 1 0 7 47 1 0 7 48 1 0 9 49 1 0 9 50 1 0 9 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 13 55 1 0 15 56 1 0 15 57 1 0 15 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 18 62 1 0 20 63 1 0 20 64 1 0 20 65 1 0 21 66 1 0 21 67 1 0 22 68 1 0 23 69 1 0 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 27 74 1 0 27 75 1 0 27 76 1 0 28 77 1 0 29 78 1 0 30 79 1 0 31 80 1 0 31 81 1 0 34 82 1 0 37 83 1 0 M END

Standard InCHIKey	OWODMVTTWPVWQA-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C30H46O7/c1-25(23(34)35)10-12-30(24(36)37)13-11-28(4)17(18(30)14-25)6-7-21-26(2)15-19(32)22(33)27(3,16-31)20(26)8-9-29(21,28)5/h6,18-22,31-33H,7-16H2,1-5H3,(H,34,35)(H,36,37)
SMILES	CC1(CCC2(CCC3(C)C(=CCC4C5(C)CC(C(C(C)(CO)C5CCC34C)O)O)C2C1)C(=O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.32	Volume:	538.276 ? Van der Waals volume.
Dense:	0.963	LogP:	2.605 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.403 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.969 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	28.0
TPSA:	135.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.353	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.042	Fsp³:	0.867
MCE-18:	111.286 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.133	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.144 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.255	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.617	MDCK Permeability:	-4.964
Pgp-inhibitor:	0.0	Pgp-substrate:	0.079
PAMPA:	1.0 ? 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):	0.075
20% Bioavailability (F20%):	0.005	30% Bioavailability (F30%):	0.003
50% Bioavailability (F50%):	0.648

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	1.0
Plasma Protein Binding (PPB):	72.146%	Volume Distribution (VD):	-0.494
Fu:	21.381% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.014
OATP1B3 inhibitor:	0.468	BCRP inhibitor:	0.0
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.962	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

1.122

Half-life (T1/2):

2.33

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.019
Human Hepatotoxicity (H-HT):	0.369	Drug-induced Liver Injury (DILI):	0.115
AMES Toxicity:	0.031	Rat Oral Acute Toxicity:	0.13
Maximum Recommended Daily Dose:	0.433	Skin Sensitization:	0.07
Carcinogencity:	0.073	Eye Corrosion:	0.0
Eye Irritation:	0.028	Respiratory Toxicity:	0.29
Drug-induced Neurotoxicity:	0.025	Ototoxicity:	0.98
Hematotoxicity:	0.105	Drug-induced Nephrotoxicity:	0.297
Genotoxicity:	0.036	RPMI-8226 Immunitoxicity:	0.013
A549 Cytotoxicity:	0.01	Hek293 Cytotoxicity:	0.036
BCF:	0.438 ? 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:	3.546 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.316 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.923 ? 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
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932140]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	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 NPC86728 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	23427
0.1-0.2	23101
0.2-0.3	2667
0.3-0.4	368
0.4-0.5	181
0.5-0.6	64
0.6-0.7	20
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8254	Intermediate Similarity	NPC231063
0.8254	Intermediate Similarity	NPC282395
0.8254	Intermediate Similarity	NPC88116
0.8254	Intermediate Similarity	NPC609452
0.7424	Intermediate Similarity	NPC173744
0.7424	Intermediate Similarity	NPC204961
0.7424	Intermediate Similarity	NPC73004
0.7424	Intermediate Similarity	NPC110308
0.7313	Intermediate Similarity	NPC32407
0.7313	Intermediate Similarity	NPC263548
0.7313	Intermediate Similarity	NPC606320
0.7206	Intermediate Similarity	NPC247139
0.7164	Intermediate Similarity	NPC472149
0.7015	Intermediate Similarity	NPC84319
0.7015	Intermediate Similarity	NPC52021
0.7015	Intermediate Similarity	NPC599947
0.7	Intermediate Similarity	NPC20235
0.7	Intermediate Similarity	NPC299996
0.6957	Remote Similarity	NPC201657
0.6812	Remote Similarity	NPC145667
0.6667	Remote Similarity	NPC479743
0.6522	Remote Similarity	NPC307282
0.6429	Remote Similarity	NPC37221
0.6286	Remote Similarity	NPC270768
0.6286	Remote Similarity	NPC59263
0.6286	Remote Similarity	NPC210106
0.6286	Remote Similarity	NPC121798
0.6286	Remote Similarity	NPC234346
0.625	Remote Similarity	NPC88847
0.6197	Remote Similarity	NPC71074
0.6197	Remote Similarity	NPC481314
0.6197	Remote Similarity	NPC605937
0.6184	Remote Similarity	NPC188833
0.6164	Remote Similarity	NPC481316
0.6111	Remote Similarity	NPC259733
0.6111	Remote Similarity	NPC158371
0.6111	Remote Similarity	NPC207922
0.6027	Remote Similarity	NPC9613
0.5972	Remote Similarity	NPC106112
0.5972	Remote Similarity	NPC261935
0.5972	Remote Similarity	NPC481360
0.5946	Remote Similarity	NPC25299
0.5946	Remote Similarity	NPC481322
0.5946	Remote Similarity	NPC130520
0.589	Remote Similarity	NPC305464
0.589	Remote Similarity	NPC19376
0.589	Remote Similarity	NPC25848
0.5833	Remote Similarity	NPC182797
0.5833	Remote Similarity	NPC52169
0.5833	Remote Similarity	NPC488562
0.5789	Remote Similarity	NPC481315
0.5769	Remote Similarity	NPC96693
0.5694	Remote Similarity	NPC480946
0.5694	Remote Similarity	NPC130577
0.5694	Remote Similarity	NPC142415
0.5694	Remote Similarity	NPC102683
0.5676	Remote Similarity	NPC40092
0.5658	Remote Similarity	NPC116457
0.5652	Remote Similarity	NPC478657
0.5616	Remote Similarity	NPC282616
0.5616	Remote Similarity	NPC229281
0.5616	Remote Similarity	NPC306541
0.56	Remote Similarity	NPC263393
0.56	Remote Similarity	NPC191412
0.56	Remote Similarity	NPC114159
0.56	Remote Similarity	NPC6818
0.5541	Remote Similarity	NPC61543
0.5541	Remote Similarity	NPC293048
0.5541	Remote Similarity	NPC225585
0.5541	Remote Similarity	NPC158141
0.5526	Remote Similarity	NPC607666
0.5526	Remote Similarity	NPC608261
0.5526	Remote Similarity	NPC611078
0.5467	Remote Similarity	NPC136697
0.5467	Remote Similarity	NPC298554
0.5455	Remote Similarity	NPC117663
0.5455	Remote Similarity	NPC481318
0.5405	Remote Similarity	NPC275809
0.5405	Remote Similarity	NPC32118
0.5352	Remote Similarity	NPC604575
0.5342	Remote Similarity	NPC43686
0.5333	Remote Similarity	NPC130278
0.5333	Remote Similarity	NPC111214
0.5325	Remote Similarity	NPC127689
0.527	Remote Similarity	NPC474806
0.527	Remote Similarity	NPC133579
0.5263	Remote Similarity	NPC87095
0.5256	Remote Similarity	NPC324063
0.525	Remote Similarity	NPC481320
0.52	Remote Similarity	NPC37038
0.5195	Remote Similarity	NPC35239
0.5185	Remote Similarity	NPC481319
0.5132	Remote Similarity	NPC271614
0.5128	Remote Similarity	NPC46441
0.5128	Remote Similarity	NPC62516
0.5067	Remote Similarity	NPC96916
0.5067	Remote Similarity	NPC187722
0.5065	Remote Similarity	NPC202728
0.5065	Remote Similarity	NPC158059
0.5065	Remote Similarity	NPC200752
0.5063	Remote Similarity	NPC174663
0.5063	Remote Similarity	NPC600832

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC86728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6418
0.1-0.2	2683
0.2-0.3	42
0.3-0.4	7
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