NPASS Compound

Structure

NPC118419 OpenBabel07101719522D 27 30 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 2 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 18 1 0 0 0 0 6 9 1 0 0 0 0 6 16 2 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 17 2 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 18 24 1 1 0 0 0 19 25 1 0 0 0 0 20 21 2 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	365.2
Volume:	391.051
LogP:	4.493
LogD:	3.914
LogS:	-4.687
# Rotatable Bonds:	5
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.781
Synthetic Accessibility Score:	2.727
Fsp3:	0.391
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	4.688180342782289e-05
Pgp-inhibitor:	0.973
Pgp-substrate:	0.622
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.966
Plasma Protein Binding (PPB):	68.22467041015625%
Volume Distribution (VD):	1.952
Pgp-substrate:	5.620820999145508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.671
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.599
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.548
CYP2D6-inhibitor:	0.97
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.493
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	10.97
Half-life (T1/2):	0.413

ADMET: Toxicity

hERG Blockers:	0.822
Human Hepatotoxicity (H-HT):	0.416
Drug-inuced Liver Injury (DILI):	0.886
AMES Toxicity:	0.45
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.857
Skin Sensitization:	0.934
Carcinogencity:	0.376
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC118419

Natural Product ID:	NPC118419
*Common Name:**	(8Ar)-7-(3,4-Dimethoxyphenyl)-6-(4-Methoxyphenyl)-1,2,3,5,8,8A-Hexahydroindolizine
IUPAC Name:	(8aR)-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizine
Synonyms:
Standard InCHIKey:	WOAHFBLGXWXVSL-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C23H27NO3/c1-25-19-9-6-16(7-10-19)21-15-24-12-4-5-18(24)14-20(21)17-8-11-22(26-2)23(13-17)27-3/h6-11,13,18H,4-5,12,14-15H2,1-3H3/p+1/t18-/m1/s1
SMILES:	COc1ccc(cc1)C1=C(C[C@H]2CCC[NH+]2C1)c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483226
PubChem CID:	637044
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO33385	cynanchum vincetoxicum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087617]
NPO33385	cynanchum vincetoxicum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]
NPO8035	Tylophora tanakae	Species	Apocynaceae	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
IC50	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2630.0	nM	PMID[568195]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2440.0	nM	PMID[568195]

☑ 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 NPC118419 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	267
0.1-0.2	1464
0.2-0.3	8153
0.3-0.4	9925
0.4-0.5	6876
0.5-0.6	11656
0.6-0.7	3393
0.7-0.8	872
0.8-0.85	73
0.85-0.9	14
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9764	High Similarity	NPC11147
0.9612	High Similarity	NPC193528
0.916	High Similarity	NPC475828
0.8769	High Similarity	NPC172403
0.875	High Similarity	NPC314682
0.8714	High Similarity	NPC95075
0.8714	High Similarity	NPC90844
0.8714	High Similarity	NPC253883
0.8686	High Similarity	NPC328750
0.8686	High Similarity	NPC188163
0.8686	High Similarity	NPC213206
0.8686	High Similarity	NPC474915
0.8592	High Similarity	NPC219162
0.8521	High Similarity	NPC475959
0.844	Intermediate Similarity	NPC185838
0.8429	Intermediate Similarity	NPC128019
0.8429	Intermediate Similarity	NPC476567
0.8429	Intermediate Similarity	NPC136860
0.8414	Intermediate Similarity	NPC26601
0.8394	Intermediate Similarity	NPC42793
0.8394	Intermediate Similarity	NPC231884
0.8394	Intermediate Similarity	NPC167944
0.8392	Intermediate Similarity	NPC130941
0.8333	Intermediate Similarity	NPC44869
0.8322	Intermediate Similarity	NPC191376
0.8322	Intermediate Similarity	NPC144863
0.8322	Intermediate Similarity	NPC179825
0.8322	Intermediate Similarity	NPC321505
0.8322	Intermediate Similarity	NPC51957
0.8322	Intermediate Similarity	NPC476151
0.8322	Intermediate Similarity	NPC106295
0.8322	Intermediate Similarity	NPC16107
0.8322	Intermediate Similarity	NPC210437
0.8322	Intermediate Similarity	NPC476144
0.8299	Intermediate Similarity	NPC76079
0.8271	Intermediate Similarity	NPC301713
0.8264	Intermediate Similarity	NPC147390
0.8264	Intermediate Similarity	NPC135538
0.8264	Intermediate Similarity	NPC24233
0.8264	Intermediate Similarity	NPC428
0.8264	Intermediate Similarity	NPC476571
0.8264	Intermediate Similarity	NPC246587
0.8264	Intermediate Similarity	NPC7467
0.8244	Intermediate Similarity	NPC298486
0.8222	Intermediate Similarity	NPC160193
0.8219	Intermediate Similarity	NPC476568
0.8207	Intermediate Similarity	NPC103379
0.8207	Intermediate Similarity	NPC477565
0.8207	Intermediate Similarity	NPC92541
0.8182	Intermediate Similarity	NPC130926
0.8182	Intermediate Similarity	NPC145304
0.8176	Intermediate Similarity	NPC41178
0.8176	Intermediate Similarity	NPC244112
0.8176	Intermediate Similarity	NPC93593
0.8176	Intermediate Similarity	NPC138487
0.8176	Intermediate Similarity	NPC216459
0.8163	Intermediate Similarity	NPC210148
0.8163	Intermediate Similarity	NPC233029
0.8121	Intermediate Similarity	NPC146288
0.8095	Intermediate Similarity	NPC81733
0.8095	Intermediate Similarity	NPC326316
0.8082	Intermediate Similarity	NPC207824
0.8082	Intermediate Similarity	NPC60538
0.8071	Intermediate Similarity	NPC95366
0.8071	Intermediate Similarity	NPC248505
0.8071	Intermediate Similarity	NPC252107
0.8062	Intermediate Similarity	NPC120075
0.8054	Intermediate Similarity	NPC78733
0.8047	Intermediate Similarity	NPC47194
0.8031	Intermediate Similarity	NPC165106
0.8029	Intermediate Similarity	NPC476570
0.8029	Intermediate Similarity	NPC114102
0.8028	Intermediate Similarity	NPC323204
0.8027	Intermediate Similarity	NPC220858
0.8027	Intermediate Similarity	NPC97221
0.8027	Intermediate Similarity	NPC88249
0.8027	Intermediate Similarity	NPC151895
0.8027	Intermediate Similarity	NPC192768
0.8015	Intermediate Similarity	NPC321133
0.8015	Intermediate Similarity	NPC155838
0.8	Intermediate Similarity	NPC234392
0.8	Intermediate Similarity	NPC186063
0.8	Intermediate Similarity	NPC145446
0.8	Intermediate Similarity	NPC137172
0.8	Intermediate Similarity	NPC180756
0.8	Intermediate Similarity	NPC31311
0.8	Intermediate Similarity	NPC99078
0.8	Intermediate Similarity	NPC7018
0.8	Intermediate Similarity	NPC147091
0.8	Intermediate Similarity	NPC323443
0.7974	Intermediate Similarity	NPC233650
0.7973	Intermediate Similarity	NPC76213
0.7973	Intermediate Similarity	NPC277669
0.7971	Intermediate Similarity	NPC214869
0.7961	Intermediate Similarity	NPC266753
0.7961	Intermediate Similarity	NPC160298
0.7961	Intermediate Similarity	NPC232924
0.7961	Intermediate Similarity	NPC306902
0.7961	Intermediate Similarity	NPC477559
0.7959	Intermediate Similarity	NPC211296
0.7956	Intermediate Similarity	NPC52029
0.7956	Intermediate Similarity	NPC195749
0.7956	Intermediate Similarity	NPC35961
0.7956	Intermediate Similarity	NPC470706
0.7943	Intermediate Similarity	NPC220923
0.7943	Intermediate Similarity	NPC253429
0.7943	Intermediate Similarity	NPC470707
0.7933	Intermediate Similarity	NPC184026
0.7933	Intermediate Similarity	NPC278799
0.7933	Intermediate Similarity	NPC2413
0.7933	Intermediate Similarity	NPC193949
0.7933	Intermediate Similarity	NPC127674
0.7933	Intermediate Similarity	NPC204828
0.7933	Intermediate Similarity	NPC189266
0.7933	Intermediate Similarity	NPC276588
0.7933	Intermediate Similarity	NPC207757
0.7933	Intermediate Similarity	NPC54379
0.7933	Intermediate Similarity	NPC5238
0.7933	Intermediate Similarity	NPC469817
0.7933	Intermediate Similarity	NPC249797
0.7933	Intermediate Similarity	NPC39701
0.7933	Intermediate Similarity	NPC172765
0.7933	Intermediate Similarity	NPC295691
0.7933	Intermediate Similarity	NPC110416
0.7929	Intermediate Similarity	NPC196609
0.7929	Intermediate Similarity	NPC96406
0.7929	Intermediate Similarity	NPC136330
0.7929	Intermediate Similarity	NPC230698
0.7929	Intermediate Similarity	NPC205178
0.7929	Intermediate Similarity	NPC255817
0.7929	Intermediate Similarity	NPC251454
0.7929	Intermediate Similarity	NPC277042
0.7929	Intermediate Similarity	NPC73883
0.7922	Intermediate Similarity	NPC134858
0.7919	Intermediate Similarity	NPC148898
0.7914	Intermediate Similarity	NPC325568
0.7907	Intermediate Similarity	NPC475815
0.7907	Intermediate Similarity	NPC473264
0.7905	Intermediate Similarity	NPC274026
0.7895	Intermediate Similarity	NPC211992
0.7895	Intermediate Similarity	NPC477080
0.7895	Intermediate Similarity	NPC111485
0.7895	Intermediate Similarity	NPC216816
0.7887	Intermediate Similarity	NPC231572
0.7881	Intermediate Similarity	NPC25084
0.7881	Intermediate Similarity	NPC477133
0.7881	Intermediate Similarity	NPC477132
0.7881	Intermediate Similarity	NPC247639
0.7879	Intermediate Similarity	NPC344161
0.7867	Intermediate Similarity	NPC477564
0.7867	Intermediate Similarity	NPC2295
0.7857	Intermediate Similarity	NPC45783
0.7857	Intermediate Similarity	NPC167096
0.7857	Intermediate Similarity	NPC94280
0.7857	Intermediate Similarity	NPC103947
0.7857	Intermediate Similarity	NPC328419
0.7857	Intermediate Similarity	NPC159150
0.7857	Intermediate Similarity	NPC193673
0.7852	Intermediate Similarity	NPC8337
0.7852	Intermediate Similarity	NPC85747
0.7846	Intermediate Similarity	NPC81067
0.7846	Intermediate Similarity	NPC9341
0.7842	Intermediate Similarity	NPC318862
0.7829	Intermediate Similarity	NPC476572
0.7821	Intermediate Similarity	NPC150879
0.7821	Intermediate Similarity	NPC210140
0.7817	Intermediate Similarity	NPC225745
0.7817	Intermediate Similarity	NPC28641
0.7817	Intermediate Similarity	NPC194359
0.7815	Intermediate Similarity	NPC187022
0.7815	Intermediate Similarity	NPC80129
0.7815	Intermediate Similarity	NPC325871
0.7815	Intermediate Similarity	NPC99659
0.781	Intermediate Similarity	NPC251571
0.781	Intermediate Similarity	NPC153990
0.7806	Intermediate Similarity	NPC238530
0.7806	Intermediate Similarity	NPC225774
0.7806	Intermediate Similarity	NPC276944
0.7806	Intermediate Similarity	NPC232514
0.7801	Intermediate Similarity	NPC180647
0.78	Intermediate Similarity	NPC82285
0.78	Intermediate Similarity	NPC133011
0.7786	Intermediate Similarity	NPC160692
0.7785	Intermediate Similarity	NPC13397
0.7785	Intermediate Similarity	NPC223125
0.7778	Intermediate Similarity	NPC470925
0.7763	Intermediate Similarity	NPC203784
0.7763	Intermediate Similarity	NPC126519
0.7763	Intermediate Similarity	NPC170503
0.7762	Intermediate Similarity	NPC210086
0.7761	Intermediate Similarity	NPC57268
0.7761	Intermediate Similarity	NPC216929
0.7761	Intermediate Similarity	NPC126935
0.7761	Intermediate Similarity	NPC172676
0.7761	Intermediate Similarity	NPC80241
0.7761	Intermediate Similarity	NPC301641
0.7761	Intermediate Similarity	NPC65933
0.7761	Intermediate Similarity	NPC312713
0.7756	Intermediate Similarity	NPC24264
0.7756	Intermediate Similarity	NPC219341

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 NPC118419 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	694
0.2-0.3	961
0.3-0.4	1967
0.4-0.5	2736
0.5-0.6	1659
0.6-0.7	762
0.7-0.8	171
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8712	High Similarity	NPD5718	Phase 2
0.8702	High Similarity	NPD5752	Clinical (unspecified phase)
0.8686	High Similarity	NPD4664	Clinical (unspecified phase)
0.8496	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD6896	Approved
0.8394	Intermediate Similarity	NPD6895	Approved
0.8369	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD4237	Approved
0.8357	Intermediate Similarity	NPD4236	Phase 3
0.8333	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD4584	Approved
0.8239	Intermediate Similarity	NPD5241	Discontinued
0.8182	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD4017	Approved
0.8042	Intermediate Similarity	NPD6331	Phase 2
0.8042	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD5283	Phase 1
0.8015	Intermediate Similarity	NPD2668	Approved
0.8015	Intermediate Similarity	NPD2667	Approved
0.7986	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD5177	Phase 3
0.7931	Intermediate Similarity	NPD7124	Phase 2
0.7929	Intermediate Similarity	NPD2492	Phase 1
0.7914	Intermediate Similarity	NPD3109	Approved
0.7914	Intermediate Similarity	NPD3110	Approved
0.7881	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD7905	Discontinued
0.7868	Intermediate Similarity	NPD7018	Phase 2
0.7852	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD3060	Approved
0.7847	Intermediate Similarity	NPD4162	Approved
0.7838	Intermediate Similarity	NPD3640	Phase 3
0.7838	Intermediate Similarity	NPD3639	Approved
0.7838	Intermediate Similarity	NPD6030	Approved
0.7838	Intermediate Similarity	NPD6031	Approved
0.7838	Intermediate Similarity	NPD3641	Approved
0.7815	Intermediate Similarity	NPD7298	Approved
0.7778	Intermediate Similarity	NPD6788	Approved
0.7746	Intermediate Similarity	NPD6111	Discontinued
0.7733	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD5976	Discontinued
0.7714	Intermediate Similarity	NPD3531	Approved
0.7714	Intermediate Similarity	NPD4474	Approved
0.7714	Intermediate Similarity	NPD4475	Approved
0.7714	Intermediate Similarity	NPD3530	Approved
0.7714	Intermediate Similarity	NPD2674	Phase 3
0.7714	Intermediate Similarity	NPD3532	Approved
0.7712	Intermediate Similarity	NPD5978	Approved
0.7712	Intermediate Similarity	NPD5977	Approved
0.771	Intermediate Similarity	NPD3596	Phase 2
0.7704	Intermediate Similarity	NPD2233	Approved
0.7704	Intermediate Similarity	NPD2232	Approved
0.7704	Intermediate Similarity	NPD2230	Approved
0.7676	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4210	Discontinued
0.7655	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5772	Approved
0.7647	Intermediate Similarity	NPD5773	Approved
0.7647	Intermediate Similarity	NPD2977	Approved
0.7647	Intermediate Similarity	NPD1669	Approved
0.7647	Intermediate Similarity	NPD2978	Approved
0.7643	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4772	Phase 2
0.7632	Intermediate Similarity	NPD6386	Approved
0.7632	Intermediate Similarity	NPD4773	Phase 2
0.7632	Intermediate Similarity	NPD6385	Approved
0.7628	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4005	Discontinued
0.7613	Intermediate Similarity	NPD7831	Phase 2
0.7613	Intermediate Similarity	NPD7833	Phase 2
0.7613	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6584	Phase 3
0.76	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6580	Approved
0.7594	Intermediate Similarity	NPD2486	Discontinued
0.7594	Intermediate Similarity	NPD6581	Approved
0.7591	Intermediate Similarity	NPD2922	Phase 1
0.7584	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3294	Phase 2
0.7552	Intermediate Similarity	NPD2653	Approved
0.7551	Intermediate Similarity	NPD5754	Discontinued
0.7537	Intermediate Similarity	NPD2594	Approved
0.7537	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD2595	Approved
0.7537	Intermediate Similarity	NPD6382	Discontinued
0.7536	Intermediate Similarity	NPD3055	Approved
0.7536	Intermediate Similarity	NPD3053	Approved
0.7536	Intermediate Similarity	NPD4098	Discontinued
0.7534	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD7037	Approved
0.7532	Intermediate Similarity	NPD4166	Phase 2
0.7532	Intermediate Similarity	NPD3051	Approved
0.7518	Intermediate Similarity	NPD5111	Phase 2
0.7518	Intermediate Similarity	NPD5110	Phase 2
0.7518	Intermediate Similarity	NPD3145	Approved
0.7518	Intermediate Similarity	NPD1420	Approved
0.7518	Intermediate Similarity	NPD3144	Approved
0.7518	Intermediate Similarity	NPD1421	Approved
0.7518	Intermediate Similarity	NPD5109	Approved
0.7517	Intermediate Similarity	NPD2161	Phase 2
0.7517	Intermediate Similarity	NPD5297	Approved
0.7516	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6873	Phase 2
0.7516	Intermediate Similarity	NPD7110	Phase 1
0.7484	Intermediate Similarity	NPD2970	Approved
0.7484	Intermediate Similarity	NPD2969	Approved
0.7484	Intermediate Similarity	NPD2560	Approved
0.7484	Intermediate Similarity	NPD2563	Approved
0.7468	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4123	Phase 3
0.7462	Intermediate Similarity	NPD4571	Approved
0.7462	Intermediate Similarity	NPD4572	Approved
0.7462	Intermediate Similarity	NPD4573	Approved
0.7451	Intermediate Similarity	NPD6876	Approved
0.7451	Intermediate Similarity	NPD6875	Approved
0.7438	Intermediate Similarity	NPD27	Approved
0.7438	Intermediate Similarity	NPD2489	Approved
0.7438	Intermediate Similarity	NPD4481	Phase 3
0.7432	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD2989	Phase 2
0.7431	Intermediate Similarity	NPD2986	Phase 2
0.7429	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD593	Approved
0.7424	Intermediate Similarity	NPD595	Approved
0.7423	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4010	Discontinued
0.7417	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3443	Approved
0.7407	Intermediate Similarity	NPD3445	Approved
0.7407	Intermediate Similarity	NPD3444	Approved
0.7407	Intermediate Similarity	NPD4093	Discontinued
0.74	Intermediate Similarity	NPD3124	Discontinued
0.7391	Intermediate Similarity	NPD6539	Approved
0.7391	Intermediate Similarity	NPD6543	Approved
0.7391	Intermediate Similarity	NPD6542	Approved
0.7391	Intermediate Similarity	NPD6582	Phase 2
0.7391	Intermediate Similarity	NPD6583	Phase 3
0.7391	Intermediate Similarity	NPD6540	Phase 3
0.7389	Intermediate Similarity	NPD5604	Discontinued
0.7388	Intermediate Similarity	NPD5536	Phase 2
0.7368	Intermediate Similarity	NPD2122	Discontinued
0.7368	Intermediate Similarity	NPD2557	Approved
0.7358	Intermediate Similarity	NPD7802	Discontinued
0.7357	Intermediate Similarity	NPD2990	Approved
0.7357	Intermediate Similarity	NPD2987	Approved
0.7351	Intermediate Similarity	NPD1424	Approved
0.7351	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1375	Discontinued
0.7346	Intermediate Similarity	NPD8099	Discontinued
0.7346	Intermediate Similarity	NPD8251	Approved
0.7346	Intermediate Similarity	NPD8252	Approved
0.7329	Intermediate Similarity	NPD2898	Approved
0.7328	Intermediate Similarity	NPD228	Approved
0.7324	Intermediate Similarity	NPD5746	Approved
0.7315	Intermediate Similarity	NPD7466	Approved
0.7312	Intermediate Similarity	NPD6071	Discontinued
0.731	Intermediate Similarity	NPD3054	Approved
0.731	Intermediate Similarity	NPD3052	Approved
0.7301	Intermediate Similarity	NPD8156	Discontinued
0.7297	Intermediate Similarity	NPD7153	Discontinued
0.7292	Intermediate Similarity	NPD2238	Phase 2
0.7289	Intermediate Similarity	NPD7280	Phase 3
0.7289	Intermediate Similarity	NPD7281	Phase 3
0.7285	Intermediate Similarity	NPD7598	Phase 2
0.7284	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3049	Approved
0.7273	Intermediate Similarity	NPD1039	Discontinued
0.7273	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4659	Approved
0.7266	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2429	Approved
0.7266	Intermediate Similarity	NPD2428	Approved
0.725	Intermediate Similarity	NPD6107	Approved
0.7244	Intermediate Similarity	NPD5720	Discontinued
0.7237	Intermediate Similarity	NPD7019	Approved
0.7237	Intermediate Similarity	NPD2874	Phase 2
0.7237	Intermediate Similarity	NPD7020	Approved
0.723	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4678	Approved
0.7226	Intermediate Similarity	NPD2556	Approved
0.7226	Intermediate Similarity	NPD4180	Approved
0.7226	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4675	Approved
0.7226	Intermediate Similarity	NPD2554	Approved
0.7226	Intermediate Similarity	NPD4179	Approved
0.7222	Intermediate Similarity	NPD7477	Discontinued
0.7222	Intermediate Similarity	NPD5745	Approved
0.7218	Intermediate Similarity	NPD2234	Approved
0.7218	Intermediate Similarity	NPD2229	Approved
0.7218	Intermediate Similarity	NPD2228	Approved
0.7214	Intermediate Similarity	NPD6541	Approved
0.7214	Intermediate Similarity	NPD6538	Approved
0.7214	Intermediate Similarity	NPD5311	Approved
0.7214	Intermediate Similarity	NPD5310	Approved
0.7211	Intermediate Similarity	NPD2156	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