NPASS Compound

Natural Product: NPC479743

Natural Product ID	NPC479743
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VOXCELRVDFPEJQ-OKSSEWIBSA-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]

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 79 83 0 0 0 0 0 0 0 0999 V2000 4.6934 -0.6729 -2.6377 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5239 -0.2934 -1.3816 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3505 -0.9181 -0.3283 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1318 -0.5489 0.8912 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1407 0.4373 1.3618 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4339 -0.1011 2.5483 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1309 -0.7851 2.4002 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2996 -0.4235 1.1830 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5963 -1.5632 0.2354 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8547 0.8678 0.7591 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0803 1.9158 0.7288 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3569 1.9247 1.0919 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8520 0.5849 0.5728 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2842 0.5586 0.2641 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2160 1.2394 1.1928 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4763 1.3187 -1.0799 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9652 1.4518 -1.3157 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7016 0.1448 -1.3533 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9907 -1.0238 -0.7764 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9288 -1.7408 0.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8508 -2.0539 -1.9219 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0646 -2.4540 -2.4182 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6818 -0.8308 -0.1721 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3275 -1.7354 0.9871 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8156 -1.7806 0.9986 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1977 -0.4427 1.4121 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4384 -0.3577 2.8853 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0788 -0.0480 -2.6808 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0622 2.1475 -2.5500 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2716 1.0530 0.3373 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5102 0.7228 -1.0977 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8872 1.9330 -1.9460 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0858 1.5035 1.9260 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0762 1.8577 3.1048 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9645 2.0500 1.0077 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4194 -1.4254 -2.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1110 -0.2360 -3.4220 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0781 -1.6367 -0.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7357 -1.0008 1.6929 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3682 0.7327 3.3203 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1650 -0.7997 3.0654 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6242 -0.5962 3.3694 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3222 -1.9036 2.4549 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2317 -1.4911 -0.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6722 -1.8244 0.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1685 -2.4586 0.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4797 2.9103 0.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5565 1.9744 2.1757 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9032 2.7751 0.6443 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3480 0.4721 -0.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1537 2.3512 0.9851 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0654 1.1502 2.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2500 0.9199 0.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0794 2.3357 -1.0247 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0508 0.7339 -1.9084 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4283 2.1667 -0.5870 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6804 0.3144 -0.8116 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8335 -1.3783 1.2285 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7297 -2.8516 0.1721 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9870 -1.6145 -0.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2809 -1.5417 -2.7547 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1972 -2.8987 -1.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9673 -2.6225 -3.3916 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9005 -1.0597 -0.9718 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7850 -1.3236 1.8677 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6739 -2.7695 0.8597 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5453 -2.5979 1.6812 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 -1.9304 -0.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1474 -1.3336 3.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5453 -0.3522 3.1366 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0179 0.4692 3.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0122 -0.3599 -2.7096 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9247 2.5842 -2.6576 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4922 2.1733 0.3771 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5663 0.3536 -1.6086 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9586 2.1504 -1.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8060 1.7122 -3.0073 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2826 2.8240 -1.6337 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4049 2.9659 1.1648 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 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 1 18 28 1 0 17 29 1 0 10 30 1 0 30 31 1 0 31 32 1 0 5 33 1 1 33 34 2 0 33 35 1 0 31 2 1 0 30 5 1 0 26 8 1 0 26 13 1 0 23 14 1 0 1 36 1 0 1 37 1 0 3 38 1 0 4 39 1 0 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 9 44 1 0 9 45 1 0 9 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 13 50 1 6 15 51 1 0 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 17 56 1 1 18 57 1 1 20 58 1 0 20 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 23 64 1 6 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 29 73 1 0 30 74 1 6 31 75 1 6 32 76 1 0 32 77 1 0 32 78 1 0 35 79 1 0 M END

Standard InCHIKey	VOXCELRVDFPEJQ-OKSSEWIBSA-N
Standard InCHI	InChI=1S/C30H44O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,9,12,18,20-24,31-33H,1,8,10-11,13-16H2,2-6H3,(H,34,35)/t18-,20+,21+,22+,23-,24+,26-,27-,28+,29+,30-/m0/s1
SMILES	C=C1C=C[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	484.32	Volume:	518.059 ? Van der Waals volume.
Dense:	0.935	LogP:	3.455 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.003 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.827 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.425	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.422	Fsp³:	0.767
MCE-18:	103.019 ? 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:	0.671	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.046 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.346	Promiscuous compounds:	0.115

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.655	MDCK Permeability:	-5.144
Pgp-inhibitor:	0.001	Pgp-substrate:	0.282
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):	0.0
20% Bioavailability (F20%):	0.157	30% Bioavailability (F30%):	0.033
50% Bioavailability (F50%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.895
Plasma Protein Binding (PPB):	77.945%	Volume Distribution (VD):	-0.295
Fu:	20.097% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.062	BCRP inhibitor:	0.112
BSEP inhibitor:	0.953

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.045
HLM stability:	0.006 ? 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):

2.436

Half-life (T1/2):

1.727

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.046
Human Hepatotoxicity (H-HT):	0.451	Drug-induced Liver Injury (DILI):	0.326
AMES Toxicity:	0.251	Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.268	Skin Sensitization:	0.96
Carcinogencity:	0.718	Eye Corrosion:	0.011
Eye Irritation:	0.658	Respiratory Toxicity:	0.736
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.879
Hematotoxicity:	0.355	Drug-induced Nephrotoxicity:	0.864
Genotoxicity:	0.332	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.05	Hek293 Cytotoxicity:	0.089
BCF:	0.603 ? 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:	3.397 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.994 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.155 ? 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
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	root	n.a.	PMID[18481026]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	root	n.a.	PMID[19336935]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32315181]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26333	Actinidia arguta	Species	Actinidiaceae	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

Activity Type	# Activity
Inhibition	1

Activity Type	# Activity
Others	1

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
NPT2	Others	Unspecified	n.a.	Inhibition	=	3.0	%	PMID[32315181]

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 NPC479743 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	24361
0.1-0.2	22242
0.2-0.3	2648
0.3-0.4	405
0.4-0.5	136
0.5-0.6	44
0.6-0.7	16
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
0.7324	Intermediate Similarity	NPC20235
0.7324	Intermediate Similarity	NPC299996
0.7143	Intermediate Similarity	NPC32407
0.7143	Intermediate Similarity	NPC263548
0.7143	Intermediate Similarity	NPC606320
0.6761	Remote Similarity	NPC231063
0.6761	Remote Similarity	NPC282395
0.6761	Remote Similarity	NPC173744
0.6761	Remote Similarity	NPC88116
0.6761	Remote Similarity	NPC204961
0.6761	Remote Similarity	NPC73004
0.6761	Remote Similarity	NPC609452
0.6575	Remote Similarity	NPC247139
0.6301	Remote Similarity	NPC37221
0.6267	Remote Similarity	NPC25299
0.6267	Remote Similarity	NPC481322
0.6133	Remote Similarity	NPC88847
0.6133	Remote Similarity	NPC201657
0.6081	Remote Similarity	NPC71074
0.6081	Remote Similarity	NPC605937
0.6	Remote Similarity	NPC145667
0.5867	Remote Similarity	NPC472149
0.5867	Remote Similarity	NPC110308
0.5789	Remote Similarity	NPC305464
0.5789	Remote Similarity	NPC19376
0.5789	Remote Similarity	NPC25848
0.5733	Remote Similarity	NPC84319
0.5733	Remote Similarity	NPC52021
0.5733	Remote Similarity	NPC599947
0.5714	Remote Similarity	NPC9613
0.5641	Remote Similarity	NPC127689
0.5584	Remote Similarity	NPC259733
0.5584	Remote Similarity	NPC158371
0.5584	Remote Similarity	NPC207922
0.557	Remote Similarity	NPC481318
0.5488	Remote Similarity	NPC481319
0.5455	Remote Similarity	NPC61543
0.5455	Remote Similarity	NPC293048
0.5455	Remote Similarity	NPC225585
0.5385	Remote Similarity	NPC40092
0.5385	Remote Similarity	NPC87095
0.5375	Remote Similarity	NPC116457
0.5366	Remote Similarity	NPC481320
0.5342	Remote Similarity	NPC478657
0.5325	Remote Similarity	NPC307282
0.5256	Remote Similarity	NPC481314
0.525	Remote Similarity	NPC481316
0.5185	Remote Similarity	NPC117663
0.5128	Remote Similarity	NPC270768
0.5128	Remote Similarity	NPC59263
0.5128	Remote Similarity	NPC210106
0.5128	Remote Similarity	NPC229281
0.5128	Remote Similarity	NPC121798
0.5128	Remote Similarity	NPC234346
0.5125	Remote Similarity	NPC191412
0.5125	Remote Similarity	NPC114159
0.5125	Remote Similarity	NPC6818
0.5122	Remote Similarity	NPC481315
0.5119	Remote Similarity	NPC188833
0.5119	Remote Similarity	NPC96693
0.5063	Remote Similarity	NPC300351
0.5062	Remote Similarity	NPC130520
0.5062	Remote Similarity	NPC607666
0.5062	Remote Similarity	NPC608261
0.5062	Remote Similarity	NPC611078

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6761
0.1-0.2	2357
0.2-0.3	29
0.3-0.4	3
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