NPASS Compound

Natural Product: NPC483414

Natural Product ID	NPC483414
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ORIAJDVKRTWESC-VWMIEOSCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10258886
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 -7.1915 0.4454 -0.0080 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5603 0.3284 1.3437 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1444 -0.8708 2.0658 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4286 -2.1289 1.7688 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9930 -2.0500 1.3955 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6628 -0.7898 0.5762 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1857 0.2837 1.3323 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3767 -0.6079 0.4039 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 -0.4402 0.1703 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2927 -1.5908 0.2953 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8020 -2.6814 0.6059 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0516 -1.4955 0.0765 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5891 -0.2796 -0.2641 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9582 -0.2173 -0.4779 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8106 -1.2860 -0.3727 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2175 -2.4960 -0.0252 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8677 -2.6089 0.1968 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2739 -3.8125 0.5427 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0301 -3.6132 0.0969 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2897 -4.4632 -1.0046 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1641 -1.2785 -0.5728 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9779 -0.1937 -0.9325 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9241 0.0282 0.2406 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1560 0.7788 -0.1376 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9287 1.4322 -1.4826 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5300 0.4425 -2.5446 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8153 1.2112 -3.6413 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6632 -0.5357 -2.0931 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1416 2.0017 -1.8738 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4264 1.8130 0.7720 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2033 0.7569 1.2147 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9087 0.2020 2.4453 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2932 -0.9689 2.6894 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1549 0.9241 3.5021 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1547 0.7740 -0.3823 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4924 0.7259 -0.1764 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2030 1.9749 -0.3392 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5067 3.1802 -0.1546 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1256 4.3638 -0.3878 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4379 4.4208 -0.8070 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1482 3.2626 -0.9988 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4877 2.0566 -0.7529 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4754 3.2610 -1.4215 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0790 5.6415 -1.0466 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7099 -3.1904 0.6157 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1168 -2.9229 0.8328 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2045 -0.5640 3.4430 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5573 -0.5512 -0.3788 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4556 0.7901 -0.7525 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0567 1.1548 0.0787 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8373 1.2205 1.9410 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1999 -0.9641 1.7341 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4671 -2.7482 2.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3801 -1.9984 2.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2839 -0.8286 -0.3708 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3635 0.7365 -0.7425 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1328 -4.3508 -0.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3228 -4.2861 -1.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3066 -5.5368 -0.6909 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5903 -4.3415 -1.8385 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3419 0.6927 -1.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1646 -0.9656 0.6534 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0388 0.1242 -0.1390 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1990 2.2442 -1.3713 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4133 -0.0314 -2.9841 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1257 1.9233 -3.1808 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2244 0.5023 -4.2623 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5505 1.7195 -4.3198 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4186 1.7881 -2.7795 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2965 2.2178 0.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1266 0.5794 3.6134 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6840 0.7427 4.4594 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1486 2.0205 3.3311 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4712 3.0882 0.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5660 5.2854 -0.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1073 1.1901 -0.9820 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6975 2.7265 -2.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3834 5.8828 -1.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8705 -3.9612 1.2455 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0782 -2.7830 0.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2456 0.4394 3.5593 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 16 19 1 0 19 20 1 0 15 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 25 29 1 0 24 30 1 0 23 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 13 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 41 43 1 0 40 44 1 0 5 45 1 0 4 46 1 0 3 47 1 0 7 2 1 0 36 9 2 0 42 37 1 0 17 12 1 0 28 22 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 1 3 52 1 6 4 53 1 1 5 54 1 1 6 55 1 6 14 56 1 0 18 57 1 0 20 58 1 0 20 59 1 0 20 60 1 0 22 61 1 6 23 62 1 1 24 63 1 6 25 64 1 1 26 65 1 6 27 66 1 0 27 67 1 0 27 68 1 0 29 69 1 0 30 70 1 0 34 71 1 0 34 72 1 0 34 73 1 0 38 74 1 0 39 75 1 0 42 76 1 0 43 77 1 0 44 78 1 0 45 79 1 0 46 80 1 0 47 81 1 0 M END

Standard InCHIKey	ORIAJDVKRTWESC-VWMIEOSCSA-N
Standard InCHI	InChI=1S/C30H34O17/c1-9-18(34)22(38)24(40)29(42-9)47-27-21(37)17-15(45-25(27)12-5-6-13(32)14(33)7-12)8-16(26(41-4)20(17)36)46-30-28(44-11(3)31)23(39)19(35)10(2)43-30/h5-10,18-19,22-24,28-30,32-36,38-40H,1-4H3/t9-,10-,18-,19-,22+,23+,24+,28+,29-,30-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(c(c2O)OC)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)OC(=O)C)oc1c1ccc(c(c1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.18	Volume:	610.359 ? Van der Waals volume.
Dense:	1.091	LogP:	0.599 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.985 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.021 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	31.0
TPSA:	264.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.117	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.943	Fsp³:	0.467
MCE-18:	127.818 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.645	Fluc inhibitor:	0.244 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.827 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.549 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.11	Promiscuous compounds:	0.411

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.086	MDCK Permeability:	-5.33
Pgp-inhibitor:	0.001	Pgp-substrate:	0.777
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):	0.114
20% Bioavailability (F20%):	0.379	30% Bioavailability (F30%):	0.889
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.365
Plasma Protein Binding (PPB):	80.762%	Volume Distribution (VD):	-0.08
Fu:	17.415% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.106
BSEP inhibitor:	0.054

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.064
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.79 ? 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):

2.433

Half-life (T1/2):

4.274

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.276
Human Hepatotoxicity (H-HT):	0.581	Drug-induced Liver Injury (DILI):	0.977
AMES Toxicity:	0.8	Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.018	Skin Sensitization:	0.999
Carcinogencity:	0.032	Eye Corrosion:	0.0
Eye Irritation:	0.044	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.977
Hematotoxicity:	0.089	Drug-induced Nephrotoxicity:	0.329
Genotoxicity:	0.886	RPMI-8226 Immunitoxicity:	0.09
A549 Cytotoxicity:	0.493	Hek293 Cytotoxicity:	0.154
BCF:	0.527 ? 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:	3.266 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.861 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.156 ? 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
NPO9114	Kalanchoe brasiliensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724848]
NPO9114	Kalanchoe brasiliensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7853000]
NPO9114	Kalanchoe brasiliensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
IC50	1

Activity Type	# Activity
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1.0	ug.mL-1	PMID[7853000]

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 NPC483414 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	16655
0.1-0.2	29989
0.2-0.3	2404
0.3-0.4	399
0.4-0.5	280
0.5-0.6	98
0.6-0.7	22
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8506	High Similarity	NPC483412
0.8125	Intermediate Similarity	NPC27640
0.7955	Intermediate Similarity	NPC483415
0.7865	Intermediate Similarity	NPC483416
0.7093	Intermediate Similarity	NPC488071
0.686	Remote Similarity	NPC305811
0.686	Remote Similarity	NPC271692
0.6771	Remote Similarity	NPC483413
0.6701	Remote Similarity	NPC470445
0.6263	Remote Similarity	NPC473073
0.625	Remote Similarity	NPC127546
0.625	Remote Similarity	NPC57625
0.625	Remote Similarity	NPC173637
0.625	Remote Similarity	NPC317489
0.625	Remote Similarity	NPC223424
0.625	Remote Similarity	NPC600591
0.6237	Remote Similarity	NPC265115
0.6222	Remote Similarity	NPC59534
0.6196	Remote Similarity	NPC605784
0.6154	Remote Similarity	NPC611303
0.6111	Remote Similarity	NPC46420
0.6111	Remote Similarity	NPC24043
0.61	Remote Similarity	NPC473071
0.6087	Remote Similarity	NPC21666
0.602	Remote Similarity	NPC126784
0.602	Remote Similarity	NPC241423
0.6	Remote Similarity	NPC158674
0.596	Remote Similarity	NPC470443
0.5957	Remote Similarity	NPC488072
0.5941	Remote Similarity	NPC470447
0.5941	Remote Similarity	NPC89127
0.59	Remote Similarity	NPC606657
0.5895	Remote Similarity	NPC95866
0.5889	Remote Similarity	NPC249281
0.587	Remote Similarity	NPC42773
0.587	Remote Similarity	NPC216496
0.587	Remote Similarity	NPC45522
0.5859	Remote Similarity	NPC64425
0.581	Remote Similarity	NPC470451
0.5806	Remote Similarity	NPC219904
0.5773	Remote Similarity	NPC480466
0.5673	Remote Similarity	NPC470446
0.567	Remote Similarity	NPC473682
0.5652	Remote Similarity	NPC136042
0.5638	Remote Similarity	NPC175107
0.5625	Remote Similarity	NPC276377
0.5625	Remote Similarity	NPC488078
0.5604	Remote Similarity	NPC111929
0.5604	Remote Similarity	NPC320283
0.5604	Remote Similarity	NPC41121
0.5591	Remote Similarity	NPC84362
0.5567	Remote Similarity	NPC116864
0.5567	Remote Similarity	NPC244776
0.5556	Remote Similarity	NPC480441
0.5556	Remote Similarity	NPC18772
0.5532	Remote Similarity	NPC117260
0.5532	Remote Similarity	NPC201292
0.5521	Remote Similarity	NPC223747
0.5521	Remote Similarity	NPC116458
0.5521	Remote Similarity	NPC246943
0.551	Remote Similarity	NPC254540
0.551	Remote Similarity	NPC251417
0.55	Remote Similarity	NPC233994
0.55	Remote Similarity	NPC203259
0.55	Remote Similarity	NPC33054
0.55	Remote Similarity	NPC176740
0.55	Remote Similarity	NPC471725
0.55	Remote Similarity	NPC134532
0.55	Remote Similarity	NPC602582
0.5472	Remote Similarity	NPC14187
0.5464	Remote Similarity	NPC355481
0.5437	Remote Similarity	NPC32641
0.5437	Remote Similarity	NPC256188
0.5437	Remote Similarity	NPC72016
0.5437	Remote Similarity	NPC35119
0.5435	Remote Similarity	NPC135599
0.5435	Remote Similarity	NPC73855
0.5435	Remote Similarity	NPC113968
0.5435	Remote Similarity	NPC328940
0.5435	Remote Similarity	NPC277174
0.5435	Remote Similarity	NPC606877
0.5426	Remote Similarity	NPC349108
0.5426	Remote Similarity	NPC603655
0.5392	Remote Similarity	NPC488073
0.5392	Remote Similarity	NPC488074
0.537	Remote Similarity	NPC473072
0.5368	Remote Similarity	NPC599850
0.5347	Remote Similarity	NPC155877
0.5347	Remote Similarity	NPC150164
0.534	Remote Similarity	NPC211532
0.534	Remote Similarity	NPC488364
0.5321	Remote Similarity	NPC173837
0.5319	Remote Similarity	NPC145038
0.5319	Remote Similarity	NPC56077
0.5319	Remote Similarity	NPC281131
0.5319	Remote Similarity	NPC253662
0.5319	Remote Similarity	NPC265530
0.5319	Remote Similarity	NPC179950
0.5319	Remote Similarity	NPC88789
0.5319	Remote Similarity	NPC491374
0.5306	Remote Similarity	NPC476215
0.5294	Remote Similarity	NPC473571
0.5294	Remote Similarity	NPC110941
0.5294	Remote Similarity	NPC186816
0.5288	Remote Similarity	NPC122467
0.5263	Remote Similarity	NPC45638
0.5243	Remote Similarity	NPC240306
0.5238	Remote Similarity	NPC142142
0.5238	Remote Similarity	NPC64755
0.5238	Remote Similarity	NPC486577
0.5213	Remote Similarity	NPC289667
0.5213	Remote Similarity	NPC19709
0.5213	Remote Similarity	NPC238376
0.5196	Remote Similarity	NPC605592
0.5146	Remote Similarity	NPC204693
0.5146	Remote Similarity	NPC35167
0.5146	Remote Similarity	NPC470444
0.5143	Remote Similarity	NPC473327
0.5104	Remote Similarity	NPC488080
0.5104	Remote Similarity	NPC169977
0.5102	Remote Similarity	NPC224530
0.51	Remote Similarity	NPC211594
0.5098	Remote Similarity	NPC267680
0.505	Remote Similarity	NPC480463
0.5046	Remote Similarity	NPC470455

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4967
0.1-0.2	4135
0.2-0.3	40
0.3-0.4	3
0.4-0.5	3
0.5-0.6	2
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
0.55	Remote Similarity	NPD6797	Phase 2
0.5481	Remote Similarity	NPD7251	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