NPASS Compound

Structure

CID119640 OpenBabel06191715472D 25 28 0 0 1 0 0 0 0 0999 V2000 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 19 1 6 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 22 1 0 0 0 0 14 25 1 0 0 0 0 15 18 1 0 0 0 0 15 23 1 1 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 4 1 1 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.13
Volume:	339.877
LogP:	3.917
LogD:	2.97
LogS:	-4.152
# Rotatable Bonds:	3
TPSA:	78.27
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	3.974
Fsp3:	0.474
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.732
MDCK Permeability:	2.4670478524058126e-05
Pgp-inhibitor:	0.922
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	86.22322845458984%
Volume Distribution (VD):	0.949
Pgp-substrate:	11.070076942443848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.701
CYP1A2-substrate:	0.708
CYP2C19-inhibitor:	0.495
CYP2C19-substrate:	0.495
CYP2C9-inhibitor:	0.341
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.434
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.545

ADMET: Excretion

Clearance (CL):	8.915
Half-life (T1/2):	0.299

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.908
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.383
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.145
Carcinogencity:	0.91
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC119640

Natural Product ID:	NPC119640
*Common Name:**	(2''r,3''r)-Epoxyangeloyldecursinol
IUPAC Name:	[(3S)-2,2-dimethyl-8-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
Synonyms:	(2'R,3'R)-Epoxyangeloyldecursinol
Standard InCHIKey:	VYFAOJIJWKADAF-RSXSOOJNSA-N
Standard InCHI:	InChI=1S/C19H20O6/c1-10-19(4,24-10)17(21)23-15-8-12-7-11-5-6-16(20)22-13(11)9-14(12)25-18(15,2)3/h5-7,9-10,15H,8H2,1-4H3/t10-,15+,19-/m1/s1
SMILES:	C[C@@H]1[C@](C)(C(=O)O[C@H]2Cc3cc4ccc(=O)oc4cc3OC2(C)C)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481656
PubChem CID:	11462054
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003486] Linear pyranocoumarins

*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
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	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	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
Others	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Activity	=	47.5	%	PMID[507660]
NPT2	Others	Unspecified	Activity	=	61.1	%	PMID[507660]
NPT2	Others	Unspecified	Activity	=	56.7	%	PMID[507660]

☑ 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 NPC119640 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	450
0.1-0.2	1748
0.2-0.3	4521
0.3-0.4	10034
0.4-0.5	8323
0.5-0.6	4501
0.6-0.7	6018
0.7-0.8	5491
0.8-0.85	1252
0.85-0.9	288
0.9-0.95	67
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC183646
0.9926	High Similarity	NPC476457
0.9412	High Similarity	NPC55615
0.9412	High Similarity	NPC160727
0.9412	High Similarity	NPC177281
0.9412	High Similarity	NPC149320
0.9412	High Similarity	NPC476455
0.9412	High Similarity	NPC128529
0.9412	High Similarity	NPC471630
0.9412	High Similarity	NPC283019
0.9407	High Similarity	NPC84894
0.9407	High Similarity	NPC267412
0.9407	High Similarity	NPC287182
0.9407	High Similarity	NPC166672
0.9407	High Similarity	NPC74655
0.9407	High Similarity	NPC195343
0.9407	High Similarity	NPC47163
0.9407	High Similarity	NPC198381
0.9407	High Similarity	NPC319859
0.9407	High Similarity	NPC164269
0.9407	High Similarity	NPC18804
0.9407	High Similarity	NPC127888
0.9407	High Similarity	NPC260265
0.9407	High Similarity	NPC100986
0.9338	High Similarity	NPC86892
0.9338	High Similarity	NPC471909
0.9338	High Similarity	NPC472424
0.9338	High Similarity	NPC281241
0.9338	High Similarity	NPC471625
0.9333	High Similarity	NPC296624
0.9333	High Similarity	NPC471910
0.9333	High Similarity	NPC318400
0.9333	High Similarity	NPC167111
0.9333	High Similarity	NPC133956
0.9333	High Similarity	NPC207002
0.9291	High Similarity	NPC76657
0.9197	High Similarity	NPC469675
0.9137	High Similarity	NPC211110
0.9124	High Similarity	NPC307412
0.9124	High Similarity	NPC55149
0.9111	High Similarity	NPC80170
0.9071	High Similarity	NPC312881
0.9051	High Similarity	NPC7526
0.9051	High Similarity	NPC222036
0.9007	High Similarity	NPC195357
0.9007	High Similarity	NPC287286
0.9007	High Similarity	NPC152771
0.9	High Similarity	NPC279573
0.8993	High Similarity	NPC283331
0.8978	High Similarity	NPC14248
0.8963	High Similarity	NPC199204
0.8929	High Similarity	NPC153818
0.8929	High Similarity	NPC232246
0.8929	High Similarity	NPC155963
0.8865	High Similarity	NPC151946
0.8857	High Similarity	NPC78746
0.8857	High Similarity	NPC224543
0.8857	High Similarity	NPC188380
0.8828	High Similarity	NPC171656
0.8815	High Similarity	NPC471826
0.8794	High Similarity	NPC184861
0.8794	High Similarity	NPC294456
0.8794	High Similarity	NPC212124
0.8794	High Similarity	NPC281014
0.8794	High Similarity	NPC225106
0.8786	High Similarity	NPC472525
0.8759	High Similarity	NPC168710
0.8723	High Similarity	NPC26954
0.8723	High Similarity	NPC38099
0.8723	High Similarity	NPC104796
0.8714	High Similarity	NPC62366
0.8714	High Similarity	NPC180716
0.8714	High Similarity	NPC224475
0.8714	High Similarity	NPC213173
0.8699	High Similarity	NPC294365
0.8686	High Similarity	NPC472519
0.8667	High Similarity	NPC111347
0.8667	High Similarity	NPC201667
0.8667	High Similarity	NPC73413
0.8652	High Similarity	NPC33986
0.8643	High Similarity	NPC31849
0.863	High Similarity	NPC85624
0.863	High Similarity	NPC469701
0.8603	High Similarity	NPC471828
0.8603	High Similarity	NPC471827
0.8601	High Similarity	NPC270256
0.8593	High Similarity	NPC472518
0.8593	High Similarity	NPC109675
0.8593	High Similarity	NPC273772
0.8591	High Similarity	NPC164299
0.8582	High Similarity	NPC50896
0.8582	High Similarity	NPC204353
0.8582	High Similarity	NPC326600
0.8582	High Similarity	NPC98179
0.8582	High Similarity	NPC253574
0.8562	High Similarity	NPC471824
0.8551	High Similarity	NPC185066
0.8551	High Similarity	NPC60704
0.8551	High Similarity	NPC139595
0.8551	High Similarity	NPC157212
0.8551	High Similarity	NPC293642
0.854	High Similarity	NPC234109
0.854	High Similarity	NPC188327
0.8533	High Similarity	NPC180351
0.8531	High Similarity	NPC471069
0.8531	High Similarity	NPC471068
0.8529	High Similarity	NPC291899
0.8529	High Similarity	NPC27671
0.8519	High Similarity	NPC248429
0.8519	High Similarity	NPC96286
0.8514	High Similarity	NPC471764
0.8514	High Similarity	NPC87950
0.8514	High Similarity	NPC296377
0.8511	High Similarity	NPC469952
0.8511	High Similarity	NPC469955
0.85	High Similarity	NPC29734
0.8472	Intermediate Similarity	NPC471070
0.8472	Intermediate Similarity	NPC471071
0.8472	Intermediate Similarity	NPC471072
0.8467	Intermediate Similarity	NPC103116
0.8456	Intermediate Similarity	NPC290605
0.8456	Intermediate Similarity	NPC154176
0.8456	Intermediate Similarity	NPC173350
0.8456	Intermediate Similarity	NPC50720
0.8456	Intermediate Similarity	NPC169510
0.844	Intermediate Similarity	NPC469956
0.844	Intermediate Similarity	NPC194277
0.844	Intermediate Similarity	NPC19157
0.8429	Intermediate Similarity	NPC113098
0.8421	Intermediate Similarity	NPC256141
0.8382	Intermediate Similarity	NPC13007
0.8382	Intermediate Similarity	NPC257188
0.8382	Intermediate Similarity	NPC150214
0.838	Intermediate Similarity	NPC163557
0.838	Intermediate Similarity	NPC469449
0.838	Intermediate Similarity	NPC55147
0.838	Intermediate Similarity	NPC54503
0.8378	Intermediate Similarity	NPC295696
0.837	Intermediate Similarity	NPC180006
0.837	Intermediate Similarity	NPC163200
0.837	Intermediate Similarity	NPC235190
0.8369	Intermediate Similarity	NPC267336
0.8369	Intermediate Similarity	NPC272650
0.8367	Intermediate Similarity	NPC229916
0.8366	Intermediate Similarity	NPC236756
0.8366	Intermediate Similarity	NPC311579
0.8366	Intermediate Similarity	NPC131725
0.8356	Intermediate Similarity	NPC472523
0.8345	Intermediate Similarity	NPC289316
0.8345	Intermediate Similarity	NPC307883
0.8345	Intermediate Similarity	NPC253616
0.8333	Intermediate Similarity	NPC471285
0.8333	Intermediate Similarity	NPC129650
0.8333	Intermediate Similarity	NPC167517
0.8322	Intermediate Similarity	NPC205361
0.8322	Intermediate Similarity	NPC131950
0.8322	Intermediate Similarity	NPC309953
0.8321	Intermediate Similarity	NPC315807
0.8312	Intermediate Similarity	NPC250769
0.8312	Intermediate Similarity	NPC295608
0.8312	Intermediate Similarity	NPC471746
0.8312	Intermediate Similarity	NPC278010
0.831	Intermediate Similarity	NPC175159
0.831	Intermediate Similarity	NPC280476
0.831	Intermediate Similarity	NPC119985
0.831	Intermediate Similarity	NPC123954
0.8309	Intermediate Similarity	NPC144418
0.8301	Intermediate Similarity	NPC288534
0.8299	Intermediate Similarity	NPC470856
0.8298	Intermediate Similarity	NPC19242
0.8288	Intermediate Similarity	NPC36414
0.8278	Intermediate Similarity	NPC211811
0.8276	Intermediate Similarity	NPC306365
0.8276	Intermediate Similarity	NPC472516
0.8276	Intermediate Similarity	NPC268081
0.8276	Intermediate Similarity	NPC14697
0.8273	Intermediate Similarity	NPC163248
0.8267	Intermediate Similarity	NPC474302
0.8264	Intermediate Similarity	NPC311430
0.8264	Intermediate Similarity	NPC229128
0.8264	Intermediate Similarity	NPC224941
0.8258	Intermediate Similarity	NPC470625
0.8252	Intermediate Similarity	NPC142563
0.8252	Intermediate Similarity	NPC141822
0.8252	Intermediate Similarity	NPC1220
0.8252	Intermediate Similarity	NPC241165
0.8252	Intermediate Similarity	NPC291551
0.8252	Intermediate Similarity	NPC36437
0.8252	Intermediate Similarity	NPC233018
0.8252	Intermediate Similarity	NPC205797
0.8252	Intermediate Similarity	NPC469965
0.8252	Intermediate Similarity	NPC472522
0.8252	Intermediate Similarity	NPC241341
0.8243	Intermediate Similarity	NPC201820
0.8239	Intermediate Similarity	NPC472517
0.8239	Intermediate Similarity	NPC173149
0.8239	Intermediate Similarity	NPC179015
0.8235	Intermediate Similarity	NPC295650
0.8231	Intermediate Similarity	NPC183642
0.8231	Intermediate Similarity	NPC136095

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 NPC119640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	977
0.2-0.3	1902
0.3-0.4	2627
0.4-0.5	1838
0.5-0.6	959
0.6-0.7	323
0.7-0.8	106
0.8-0.85	26
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8487	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8301	Intermediate Similarity	NPD6801	Discontinued
0.8252	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD5124	Phase 1
0.8133	Intermediate Similarity	NPD6799	Approved
0.8027	Intermediate Similarity	NPD2796	Approved
0.7987	Intermediate Similarity	NPD1652	Phase 2
0.7974	Intermediate Similarity	NPD5403	Approved
0.7962	Intermediate Similarity	NPD3817	Phase 2
0.7961	Intermediate Similarity	NPD5401	Approved
0.7961	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6599	Discontinued
0.7925	Intermediate Similarity	NPD919	Approved
0.7857	Intermediate Similarity	NPD920	Approved
0.7848	Intermediate Similarity	NPD5402	Approved
0.7821	Intermediate Similarity	NPD4380	Phase 2
0.7786	Intermediate Similarity	NPD422	Phase 1
0.7785	Intermediate Similarity	NPD7819	Suspended
0.7771	Intermediate Similarity	NPD7411	Suspended
0.7758	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1243	Approved
0.7727	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD3748	Approved
0.7712	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6798	Discontinued
0.7671	Intermediate Similarity	NPD1296	Phase 2
0.7655	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5494	Approved
0.764	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1653	Approved
0.7578	Intermediate Similarity	NPD7768	Phase 2
0.7566	Intermediate Similarity	NPD1549	Phase 2
0.7566	Intermediate Similarity	NPD2424	Discontinued
0.7564	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5844	Phase 1
0.7534	Intermediate Similarity	NPD6832	Phase 2
0.7517	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1934	Approved
0.7483	Intermediate Similarity	NPD7033	Discontinued
0.7469	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3750	Approved
0.745	Intermediate Similarity	NPD4060	Phase 1
0.7417	Intermediate Similarity	NPD7097	Phase 1
0.7415	Intermediate Similarity	NPD4908	Phase 1
0.7412	Intermediate Similarity	NPD6559	Discontinued
0.7407	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4340	Discontinued
0.7381	Intermediate Similarity	NPD3751	Discontinued
0.7368	Intermediate Similarity	NPD1510	Phase 2
0.7368	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6166	Phase 2
0.7365	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7095	Approved
0.7365	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3882	Suspended
0.7353	Intermediate Similarity	NPD6797	Phase 2
0.7349	Intermediate Similarity	NPD3787	Discontinued
0.7333	Intermediate Similarity	NPD4307	Phase 2
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1358	Approved
0.7333	Intermediate Similarity	NPD1613	Approved
0.7329	Intermediate Similarity	NPD2797	Approved
0.7329	Intermediate Similarity	NPD3267	Approved
0.7329	Intermediate Similarity	NPD3266	Approved
0.7324	Intermediate Similarity	NPD5691	Approved
0.732	Intermediate Similarity	NPD1551	Phase 2
0.732	Intermediate Similarity	NPD2935	Discontinued
0.7319	Intermediate Similarity	NPD5535	Approved
0.7315	Intermediate Similarity	NPD2313	Discontinued
0.7312	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7251	Discontinued
0.7292	Intermediate Similarity	NPD1610	Phase 2
0.7285	Intermediate Similarity	NPD1933	Approved
0.7285	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1019	Discontinued
0.7267	Intermediate Similarity	NPD7808	Phase 3
0.726	Intermediate Similarity	NPD3225	Approved
0.7255	Intermediate Similarity	NPD2799	Discontinued
0.7254	Intermediate Similarity	NPD1548	Phase 1
0.7248	Intermediate Similarity	NPD2598	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4628	Phase 3
0.7244	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2801	Approved
0.7233	Intermediate Similarity	NPD1512	Approved
0.7226	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3749	Approved
0.72	Intermediate Similarity	NPD3268	Approved
0.7197	Intermediate Similarity	NPD3887	Approved
0.7185	Intermediate Similarity	NPD9697	Approved
0.7181	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3818	Discontinued
0.7172	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2533	Approved
0.717	Intermediate Similarity	NPD2532	Approved
0.717	Intermediate Similarity	NPD2534	Approved
0.7161	Intermediate Similarity	NPD5763	Approved
0.7161	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD4062	Phase 3
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD8651	Approved
0.7143	Intermediate Similarity	NPD6232	Discontinued
0.7135	Intermediate Similarity	NPD7054	Approved
0.7134	Intermediate Similarity	NPD8455	Phase 2
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7132	Intermediate Similarity	NPD3134	Approved
0.7123	Intermediate Similarity	NPD9717	Approved
0.7115	Intermediate Similarity	NPD2897	Discontinued
0.7114	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1511	Approved
0.7105	Intermediate Similarity	NPD1240	Approved
0.7103	Intermediate Similarity	NPD3496	Discontinued
0.7101	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7472	Approved
0.7093	Intermediate Similarity	NPD7074	Phase 3
0.7086	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6959	Discontinued
0.7081	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4749	Approved
0.7072	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7549	Discontinued
0.7059	Intermediate Similarity	NPD447	Suspended
0.7055	Intermediate Similarity	NPD1091	Approved
0.7051	Intermediate Similarity	NPD6004	Phase 3
0.7051	Intermediate Similarity	NPD2346	Discontinued
0.7051	Intermediate Similarity	NPD6002	Phase 3
0.7051	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6005	Phase 3
0.7051	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4626	Approved
0.7021	Intermediate Similarity	NPD1241	Discontinued
0.702	Intermediate Similarity	NPD3027	Phase 3
0.7019	Intermediate Similarity	NPD5049	Phase 3
0.7018	Intermediate Similarity	NPD7473	Discontinued
0.7013	Intermediate Similarity	NPD1607	Approved
0.7	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3926	Phase 2
0.6994	Remote Similarity	NPD3226	Approved
0.6988	Remote Similarity	NPD2415	Discontinued
0.6981	Remote Similarity	NPD6190	Approved
0.698	Remote Similarity	NPD987	Approved
0.698	Remote Similarity	NPD1203	Approved
0.6974	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.697	Remote Similarity	NPD37	Approved
0.6968	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4536	Approved
0.6968	Remote Similarity	NPD4538	Approved
0.6966	Remote Similarity	NPD5585	Approved
0.6962	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2800	Approved
0.6959	Remote Similarity	NPD2403	Approved
0.6954	Remote Similarity	NPD5953	Discontinued
0.6946	Remote Similarity	NPD4965	Approved
0.6946	Remote Similarity	NPD4967	Phase 2
0.6946	Remote Similarity	NPD4966	Approved
0.6943	Remote Similarity	NPD2353	Approved
0.6943	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7229	Phase 3
0.6939	Remote Similarity	NPD1611	Approved
0.6937	Remote Similarity	NPD5058	Phase 3
0.6936	Remote Similarity	NPD7286	Phase 2
0.6928	Remote Similarity	NPD1465	Phase 2
0.6923	Remote Similarity	NPD5960	Phase 3
0.6918	Remote Similarity	NPD1778	Approved
0.6914	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5889	Approved
0.6909	Remote Similarity	NPD5890	Approved
0.6906	Remote Similarity	NPD2684	Approved
0.6899	Remote Similarity	NPD4534	Discontinued
0.689	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2861	Phase 2
0.6886	Remote Similarity	NPD4288	Approved
0.6886	Remote Similarity	NPD5353	Approved
0.6882	Remote Similarity	NPD8127	Discontinued
0.6882	Remote Similarity	NPD7199	Phase 2
0.6879	Remote Similarity	NPD2438	Suspended
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD6099	Approved
0.6879	Remote Similarity	NPD6032	Approved
0.6864	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6234	Discontinued
0.6863	Remote Similarity	NPD1048	Approved
0.6863	Remote Similarity	NPD7985	Registered
0.6852	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6585	Discontinued

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