NPASS Compound

Structure

NPC472508 OpenBabel07101718282D 39 41 0 0 1 0 0 0 0 0999 V2000 -4.4432 -2.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0707 1.2573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5707 0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0074 5.7616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4726 0.7573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3386 1.2573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8075 -2.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5417 -0.6081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2047 -0.2427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3979 5.9199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1398 4.2072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2581 1.7127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4877 -1.7316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4726 -0.2427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2047 0.7573 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3386 -0.7427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8103 -2.3899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2470 -1.5637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6235 0.7818 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0326 6.8508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5163 3.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6123 0.6328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9777 -0.2981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3542 -1.0799 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3653 -0.9309 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0707 1.2573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7744 5.1381 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.3103 -3.2559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6561 7.6327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0438 6.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4725 3.5745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2358 1.4146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9665 -0.4471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7195 -2.0108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0707 2.2573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1564 4.7728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8816 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2581 -1.7127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 14 1 0 0 0 0 8 18 2 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 10 27 1 0 0 0 0 11 21 1 0 0 0 0 11 27 1 0 0 0 0 12 37 1 0 0 0 0 13 16 1 0 0 0 0 14 16 2 0 0 0 0 15 26 1 6 0 0 0 17 18 1 0 0 0 0 17 28 2 0 0 0 0 18 38 1 0 0 0 0 19 12 1 6 0 0 0 19 22 1 0 0 0 0 19 39 1 0 0 0 0 20 29 2 0 0 0 0 20 30 1 0 0 0 0 21 31 2 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 32 1 1 0 0 0 23 24 1 0 0 0 0 23 33 1 6 0 0 0 24 25 1 0 0 0 0 24 34 1 1 0 0 0 25 38 1 6 0 0 0 25 39 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.24
Volume:	539.543
LogP:	0.083
LogD:	-0.221
LogS:	-2.844
# Rotatable Bonds:	10
TPSA:	200.28
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.216
Synthetic Accessibility Score:	4.646
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.0
MDCK Permeability:	9.470984514337033e-05
Pgp-inhibitor:	0.104
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.901
20% Bioavailability (F20%):	0.148
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	73.1845932006836%
Volume Distribution (VD):	0.196
Pgp-substrate:	13.42752742767334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.031

ADMET: Excretion

Clearance (CL):	1.966
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.12
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.033
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.004

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC472508

Natural Product ID:	NPC472508
*Common Name:**	VHEIRYSOAGPSSD-TWMDVTLASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VHEIRYSOAGPSSD-TWMDVTLASA-N
Standard InCHI:	InChI=1S/C27H38O12/c1-13-7-17(28)18(8-14-5-6-15(9-16(13)14)26(2,3)35)38-25-24(34)23(33)22(32)19(39-25)12-37-21(31)11-27(4,36)10-20(29)30/h7-8,15,19,22-25,32-36H,5-6,9-12H2,1-4H3,(H,29,30)/t15-,19-,22-,23+,24-,25-,27?/m1/s1
SMILES:	CC1=CC(=O)C(=CC2=C1CC(CC2)C(C)(C)O)OC3C(C(C(C(O3)COC(=O)CC(C)(CC(=O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426556
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32551	liriosma ovata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18197604]
NPO32551	liriosma ovata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25587934]

☑ 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	NP ID	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	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	50000.0	nM	PMID[495204]
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	>	50000.0	nM	PMID[495204]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC472508 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	1274
0.2-0.3	2946
0.3-0.4	6265
0.4-0.5	10679
0.5-0.6	7254
0.6-0.7	8172
0.7-0.8	5677
0.8-0.85	89
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9802	High Similarity	NPC472507
0.7822	Intermediate Similarity	NPC477746
0.7822	Intermediate Similarity	NPC477747
0.7788	Intermediate Similarity	NPC23497
0.7757	Intermediate Similarity	NPC256230
0.775	Intermediate Similarity	NPC216866
0.7714	Intermediate Similarity	NPC477749
0.7705	Intermediate Similarity	NPC198714
0.7692	Intermediate Similarity	NPC31797
0.7686	Intermediate Similarity	NPC238005
0.7686	Intermediate Similarity	NPC141196
0.7686	Intermediate Similarity	NPC1980
0.7647	Intermediate Similarity	NPC319570
0.7642	Intermediate Similarity	NPC61201
0.7619	Intermediate Similarity	NPC202886
0.7596	Intermediate Similarity	NPC471756
0.7596	Intermediate Similarity	NPC471755
0.7583	Intermediate Similarity	NPC472076
0.7583	Intermediate Similarity	NPC472075
0.7581	Intermediate Similarity	NPC475636
0.7581	Intermediate Similarity	NPC295220
0.7563	Intermediate Similarity	NPC297179
0.7563	Intermediate Similarity	NPC13710
0.7547	Intermediate Similarity	NPC472199
0.7541	Intermediate Similarity	NPC472078
0.7541	Intermediate Similarity	NPC472077
0.7524	Intermediate Similarity	NPC477748
0.7521	Intermediate Similarity	NPC42675
0.7521	Intermediate Similarity	NPC275675
0.7521	Intermediate Similarity	NPC473228
0.7521	Intermediate Similarity	NPC470829
0.752	Intermediate Similarity	NPC309096
0.752	Intermediate Similarity	NPC54614
0.7519	Intermediate Similarity	NPC596
0.75	Intermediate Similarity	NPC127530
0.75	Intermediate Similarity	NPC108141
0.748	Intermediate Similarity	NPC177820
0.748	Intermediate Similarity	NPC30188
0.748	Intermediate Similarity	NPC7850
0.748	Intermediate Similarity	NPC6615
0.7479	Intermediate Similarity	NPC309433
0.7478	Intermediate Similarity	NPC133625
0.7477	Intermediate Similarity	NPC478037
0.7477	Intermediate Similarity	NPC478036
0.746	Intermediate Similarity	NPC213634
0.7459	Intermediate Similarity	NPC471965
0.7455	Intermediate Similarity	NPC56071
0.7455	Intermediate Similarity	NPC70733
0.7453	Intermediate Similarity	NPC473311
0.7453	Intermediate Similarity	NPC303451
0.7453	Intermediate Similarity	NPC6414
0.7453	Intermediate Similarity	NPC117596
0.7442	Intermediate Similarity	NPC141215
0.7442	Intermediate Similarity	NPC190065
0.7442	Intermediate Similarity	NPC471089
0.7436	Intermediate Similarity	NPC66108
0.7431	Intermediate Similarity	NPC288350
0.7431	Intermediate Similarity	NPC173329
0.7419	Intermediate Similarity	NPC222307
0.7419	Intermediate Similarity	NPC93368
0.7419	Intermediate Similarity	NPC87662
0.7417	Intermediate Similarity	NPC176005
0.7414	Intermediate Similarity	NPC89408
0.7411	Intermediate Similarity	NPC476126
0.7411	Intermediate Similarity	NPC476235
0.7407	Intermediate Similarity	NPC472198
0.7398	Intermediate Similarity	NPC262199
0.7398	Intermediate Similarity	NPC202666
0.7398	Intermediate Similarity	NPC14617
0.7398	Intermediate Similarity	NPC471961
0.7398	Intermediate Similarity	NPC471964
0.7398	Intermediate Similarity	NPC227397
0.7395	Intermediate Similarity	NPC134869
0.7395	Intermediate Similarity	NPC152199
0.7395	Intermediate Similarity	NPC235539
0.7391	Intermediate Similarity	NPC327106
0.7391	Intermediate Similarity	NPC473288
0.7387	Intermediate Similarity	NPC469870
0.7387	Intermediate Similarity	NPC469871
0.7387	Intermediate Similarity	NPC324667
0.7385	Intermediate Similarity	NPC295885
0.7385	Intermediate Similarity	NPC140045
0.7377	Intermediate Similarity	NPC75417
0.7368	Intermediate Similarity	NPC469852
0.7364	Intermediate Similarity	NPC278506
0.7364	Intermediate Similarity	NPC476612
0.7364	Intermediate Similarity	NPC262813
0.7364	Intermediate Similarity	NPC476613
0.736	Intermediate Similarity	NPC152091
0.7355	Intermediate Similarity	NPC279143
0.7355	Intermediate Similarity	NPC470777
0.7339	Intermediate Similarity	NPC170204
0.7339	Intermediate Similarity	NPC190846
0.7339	Intermediate Similarity	NPC470922
0.7339	Intermediate Similarity	NPC277191
0.7339	Intermediate Similarity	NPC469841
0.7339	Intermediate Similarity	NPC247315
0.7339	Intermediate Similarity	NPC471962
0.7339	Intermediate Similarity	NPC469842
0.7339	Intermediate Similarity	NPC469543
0.7339	Intermediate Similarity	NPC471963
0.7339	Intermediate Similarity	NPC101051
0.7333	Intermediate Similarity	NPC23046
0.7333	Intermediate Similarity	NPC224121
0.7327	Intermediate Similarity	NPC100697
0.7321	Intermediate Similarity	NPC476246
0.7321	Intermediate Similarity	NPC477870
0.7321	Intermediate Similarity	NPC476611
0.7321	Intermediate Similarity	NPC476213
0.7321	Intermediate Similarity	NPC477871
0.7317	Intermediate Similarity	NPC275343
0.7317	Intermediate Similarity	NPC287236
0.7315	Intermediate Similarity	NPC472195
0.7315	Intermediate Similarity	NPC238090
0.7315	Intermediate Similarity	NPC320552
0.7315	Intermediate Similarity	NPC472196
0.7311	Intermediate Similarity	NPC474906
0.7311	Intermediate Similarity	NPC18547
0.7308	Intermediate Similarity	NPC251998
0.7304	Intermediate Similarity	NPC469853
0.7304	Intermediate Similarity	NPC474285
0.7304	Intermediate Similarity	NPC254538
0.7302	Intermediate Similarity	NPC270109
0.7297	Intermediate Similarity	NPC472015
0.729	Intermediate Similarity	NPC327253
0.7281	Intermediate Similarity	NPC264584
0.7281	Intermediate Similarity	NPC86095
0.728	Intermediate Similarity	NPC469947
0.728	Intermediate Similarity	NPC285091
0.728	Intermediate Similarity	NPC181066
0.7273	Intermediate Similarity	NPC188667
0.7273	Intermediate Similarity	NPC286347
0.7273	Intermediate Similarity	NPC241911
0.7273	Intermediate Similarity	NPC234522
0.7273	Intermediate Similarity	NPC475309
0.7273	Intermediate Similarity	NPC17772
0.7273	Intermediate Similarity	NPC204552
0.7266	Intermediate Similarity	NPC100390
0.7266	Intermediate Similarity	NPC254614
0.7265	Intermediate Similarity	NPC127153
0.7257	Intermediate Similarity	NPC195510
0.7257	Intermediate Similarity	NPC223834
0.7257	Intermediate Similarity	NPC222062
0.7257	Intermediate Similarity	NPC471599
0.7257	Intermediate Similarity	NPC13171
0.7248	Intermediate Similarity	NPC96736
0.7248	Intermediate Similarity	NPC159698
0.7248	Intermediate Similarity	NPC178949
0.7244	Intermediate Similarity	NPC470913
0.7244	Intermediate Similarity	NPC477077
0.7244	Intermediate Similarity	NPC477076
0.7244	Intermediate Similarity	NPC477079
0.7241	Intermediate Similarity	NPC473807
0.7236	Intermediate Similarity	NPC278163
0.7236	Intermediate Similarity	NPC187950
0.7232	Intermediate Similarity	NPC306344
0.7232	Intermediate Similarity	NPC22149
0.7232	Intermediate Similarity	NPC255677
0.7227	Intermediate Similarity	NPC101965
0.7227	Intermediate Similarity	NPC198539
0.7227	Intermediate Similarity	NPC7921
0.7227	Intermediate Similarity	NPC208998
0.7227	Intermediate Similarity	NPC326264
0.7227	Intermediate Similarity	NPC101400
0.7222	Intermediate Similarity	NPC472125
0.7222	Intermediate Similarity	NPC472197
0.7222	Intermediate Similarity	NPC472126
0.7222	Intermediate Similarity	NPC472124
0.7213	Intermediate Similarity	NPC35405
0.7213	Intermediate Similarity	NPC178548
0.7213	Intermediate Similarity	NPC473884
0.7213	Intermediate Similarity	NPC11551
0.7213	Intermediate Similarity	NPC472949
0.7213	Intermediate Similarity	NPC208381
0.7213	Intermediate Similarity	NPC473920
0.7213	Intermediate Similarity	NPC475171
0.7213	Intermediate Similarity	NPC214484
0.7213	Intermediate Similarity	NPC39211
0.7213	Intermediate Similarity	NPC469488
0.7213	Intermediate Similarity	NPC6377
0.7213	Intermediate Similarity	NPC309780
0.7213	Intermediate Similarity	NPC180550
0.7213	Intermediate Similarity	NPC114441
0.7213	Intermediate Similarity	NPC157868
0.7213	Intermediate Similarity	NPC258592
0.7213	Intermediate Similarity	NPC469945
0.7209	Intermediate Similarity	NPC478151
0.7207	Intermediate Similarity	NPC474194
0.72	Intermediate Similarity	NPC24651
0.72	Intermediate Similarity	NPC23275
0.72	Intermediate Similarity	NPC475194
0.7193	Intermediate Similarity	NPC197541
0.7193	Intermediate Similarity	NPC267869
0.7193	Intermediate Similarity	NPC469980
0.7193	Intermediate Similarity	NPC197736
0.7193	Intermediate Similarity	NPC234304
0.7193	Intermediate Similarity	NPC118761
0.7193	Intermediate Similarity	NPC151516
0.7193	Intermediate Similarity	NPC284929
0.7193	Intermediate Similarity	NPC104161

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	864
0.2-0.3	1758
0.3-0.4	2546
0.4-0.5	2118
0.5-0.6	1072
0.6-0.7	402
0.7-0.8	105
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7398	Intermediate Similarity	NPD8328	Phase 3
0.7143	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8517	Approved
0.7097	Intermediate Similarity	NPD8515	Approved
0.7097	Intermediate Similarity	NPD8513	Phase 3
0.7097	Intermediate Similarity	NPD8516	Approved
0.7094	Intermediate Similarity	NPD6686	Approved
0.7049	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6370	Approved
0.704	Intermediate Similarity	NPD8080	Discontinued
0.7031	Intermediate Similarity	NPD7736	Approved
0.7009	Intermediate Similarity	NPD6412	Phase 2
0.696	Remote Similarity	NPD7503	Approved
0.6953	Remote Similarity	NPD8293	Discontinued
0.6929	Remote Similarity	NPD7492	Approved
0.6909	Remote Similarity	NPD7983	Approved
0.688	Remote Similarity	NPD6319	Approved
0.688	Remote Similarity	NPD6054	Approved
0.6875	Remote Similarity	NPD6616	Approved
0.6855	Remote Similarity	NPD7641	Discontinued
0.6825	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7078	Approved
0.6818	Remote Similarity	NPD46	Approved
0.6818	Remote Similarity	NPD6698	Approved
0.6792	Remote Similarity	NPD6110	Phase 1
0.6746	Remote Similarity	NPD6059	Approved
0.6723	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6882	Approved
0.6719	Remote Similarity	NPD7829	Approved
0.6719	Remote Similarity	NPD7830	Approved
0.6693	Remote Similarity	NPD6015	Approved
0.6693	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6641	Remote Similarity	NPD5988	Approved
0.664	Remote Similarity	NPD6009	Approved
0.6637	Remote Similarity	NPD5282	Discontinued
0.6618	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7319	Approved
0.6585	Remote Similarity	NPD8297	Approved
0.6577	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6101	Approved
0.6565	Remote Similarity	NPD8074	Phase 3
0.6562	Remote Similarity	NPD8444	Approved
0.6557	Remote Similarity	NPD6371	Approved
0.6549	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD5778	Approved
0.6522	Remote Similarity	NPD7839	Suspended
0.6508	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7507	Approved
0.6462	Remote Similarity	NPD7642	Approved
0.646	Remote Similarity	NPD6411	Approved
0.6452	Remote Similarity	NPD6053	Discontinued
0.6412	Remote Similarity	NPD8340	Approved
0.6412	Remote Similarity	NPD8341	Approved
0.6412	Remote Similarity	NPD8342	Approved
0.6412	Remote Similarity	NPD8299	Approved
0.64	Remote Similarity	NPD4632	Approved
0.6393	Remote Similarity	NPD6899	Approved
0.6393	Remote Similarity	NPD6881	Approved
0.6391	Remote Similarity	NPD8336	Approved
0.6391	Remote Similarity	NPD8337	Approved
0.6371	Remote Similarity	NPD6650	Approved
0.6371	Remote Similarity	NPD6649	Approved
0.637	Remote Similarity	NPD7260	Phase 2
0.6364	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD5739	Approved
0.6364	Remote Similarity	NPD8451	Approved
0.6364	Remote Similarity	NPD7128	Approved
0.6364	Remote Similarity	NPD6402	Approved
0.6341	Remote Similarity	NPD6372	Approved
0.6341	Remote Similarity	NPD6373	Approved
0.6328	Remote Similarity	NPD7328	Approved
0.6328	Remote Similarity	NPD7327	Approved
0.6325	Remote Similarity	NPD6084	Phase 2
0.6325	Remote Similarity	NPD6083	Phase 2
0.6316	Remote Similarity	NPD8448	Approved
0.6311	Remote Similarity	NPD5697	Approved
0.6308	Remote Similarity	NPD8033	Approved
0.629	Remote Similarity	NPD6883	Approved
0.629	Remote Similarity	NPD7102	Approved
0.629	Remote Similarity	NPD7290	Approved
0.6279	Remote Similarity	NPD7516	Approved
0.6269	Remote Similarity	NPD6033	Approved
0.626	Remote Similarity	NPD7320	Approved
0.626	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6847	Approved
0.624	Remote Similarity	NPD6617	Approved
0.624	Remote Similarity	NPD6869	Approved
0.624	Remote Similarity	NPD8130	Phase 1
0.6231	Remote Similarity	NPD8294	Approved
0.6231	Remote Similarity	NPD8377	Approved
0.6212	Remote Similarity	NPD7604	Phase 2
0.621	Remote Similarity	NPD6012	Approved
0.621	Remote Similarity	NPD6013	Approved
0.621	Remote Similarity	NPD6014	Approved
0.6183	Remote Similarity	NPD8296	Approved
0.6183	Remote Similarity	NPD8335	Approved
0.6183	Remote Similarity	NPD8380	Approved
0.6183	Remote Similarity	NPD5983	Phase 2
0.6183	Remote Similarity	NPD8379	Approved
0.6183	Remote Similarity	NPD8378	Approved
0.6179	Remote Similarity	NPD5701	Approved
0.6176	Remote Similarity	NPD8391	Approved
0.6176	Remote Similarity	NPD8390	Approved
0.6176	Remote Similarity	NPD8392	Approved
0.6176	Remote Similarity	NPD5956	Approved
0.6174	Remote Similarity	NPD7637	Suspended
0.616	Remote Similarity	NPD4634	Approved
0.6154	Remote Similarity	NPD5695	Phase 3
0.6142	Remote Similarity	NPD8133	Approved
0.6134	Remote Similarity	NPD5696	Approved
0.6134	Remote Similarity	NPD4225	Approved
0.6129	Remote Similarity	NPD6011	Approved
0.6124	Remote Similarity	NPD7115	Discovery
0.6119	Remote Similarity	NPD6336	Discontinued
0.6087	Remote Similarity	NPD6845	Suspended
0.6075	Remote Similarity	NPD4756	Discovery
0.6033	Remote Similarity	NPD5344	Discontinued
0.6017	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD8338	Approved
0.5965	Remote Similarity	NPD4251	Approved
0.5965	Remote Similarity	NPD4250	Approved
0.595	Remote Similarity	NPD6648	Approved
0.5923	Remote Similarity	NPD6274	Approved
0.5913	Remote Similarity	NPD5737	Approved
0.5913	Remote Similarity	NPD6672	Approved
0.5909	Remote Similarity	NPD7100	Approved
0.5909	Remote Similarity	NPD7101	Approved
0.5909	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6050	Approved
0.5878	Remote Similarity	NPD7500	Approved
0.5877	Remote Similarity	NPD4249	Approved
0.5868	Remote Similarity	NPD7638	Approved
0.5865	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5369	Approved
0.5852	Remote Similarity	NPD6067	Discontinued
0.5847	Remote Similarity	NPD6399	Phase 3
0.5833	Remote Similarity	NPD6335	Approved
0.5827	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD6921	Approved
0.582	Remote Similarity	NPD7640	Approved
0.582	Remote Similarity	NPD4696	Approved
0.582	Remote Similarity	NPD5285	Approved
0.582	Remote Similarity	NPD7639	Approved
0.582	Remote Similarity	NPD5286	Approved
0.5818	Remote Similarity	NPD7329	Approved
0.5812	Remote Similarity	NPD5692	Phase 3
0.5804	Remote Similarity	NPD6435	Approved
0.5798	Remote Similarity	NPD7748	Approved
0.5789	Remote Similarity	NPD5363	Approved
0.5789	Remote Similarity	NPD1696	Phase 3
0.5785	Remote Similarity	NPD7902	Approved
0.5785	Remote Similarity	NPD4755	Approved
0.5766	Remote Similarity	NPD8273	Phase 1
0.5766	Remote Similarity	NPD4695	Discontinued
0.5763	Remote Similarity	NPD5694	Approved
0.5763	Remote Similarity	NPD7515	Phase 2
0.5758	Remote Similarity	NPD6317	Approved
0.5752	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7154	Phase 3
0.5752	Remote Similarity	NPD3669	Approved
0.575	Remote Similarity	NPD4629	Approved
0.575	Remote Similarity	NPD5210	Approved
0.5739	Remote Similarity	NPD5279	Phase 3
0.5734	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD7799	Discontinued
0.5726	Remote Similarity	NPD8085	Approved
0.5726	Remote Similarity	NPD8083	Approved
0.5726	Remote Similarity	NPD5226	Approved
0.5726	Remote Similarity	NPD8138	Approved
0.5726	Remote Similarity	NPD6673	Approved
0.5726	Remote Similarity	NPD5224	Approved
0.5726	Remote Similarity	NPD6080	Approved
0.5726	Remote Similarity	NPD8086	Approved
0.5726	Remote Similarity	NPD8139	Approved
0.5726	Remote Similarity	NPD8084	Approved
0.5726	Remote Similarity	NPD4753	Phase 2
0.5726	Remote Similarity	NPD8082	Approved
0.5726	Remote Similarity	NPD5225	Approved
0.5726	Remote Similarity	NPD5211	Phase 2
0.5726	Remote Similarity	NPD6904	Approved
0.5726	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD6314	Approved
0.5714	Remote Similarity	NPD6313	Approved
0.5714	Remote Similarity	NPD6914	Discontinued
0.5704	Remote Similarity	NPD6908	Approved
0.5704	Remote Similarity	NPD6909	Approved
0.5691	Remote Similarity	NPD4700	Approved
0.569	Remote Similarity	NPD7524	Approved
0.5682	Remote Similarity	NPD6868	Approved
0.568	Remote Similarity	NPD8275	Approved
0.568	Remote Similarity	NPD8276	Approved
0.568	Remote Similarity	NPD5175	Approved
0.568	Remote Similarity	NPD1407	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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