NPASS Compound

Structure

NPC11147 OpenBabel07101718282D 29 32 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 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 5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 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 1.7321 -1.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 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 0.5000 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 -1.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 18 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 25 1 0 0 0 0 12 16 2 0 0 0 0 12 23 1 0 0 0 0 13 17 2 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 25 1 1 0 0 0 19 20 2 0 0 0 0 21 23 2 0 0 0 0 21 26 1 0 0 0 0 22 24 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	395.21
Volume:	417.137
LogP:	4.199
LogD:	3.82
LogS:	-4.38
# Rotatable Bonds:	6
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	2.811
Fsp3:	0.417
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:	-4.862
MDCK Permeability:	5.454631173051894e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.367

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95
Plasma Protein Binding (PPB):	61.899391174316406%
Volume Distribution (VD):	1.822
Pgp-substrate:	10.902501106262207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.469
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.373
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.596
CYP2D6-inhibitor:	0.865
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.631
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	10.52
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.655
Human Hepatotoxicity (H-HT):	0.378
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.169
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.928
Carcinogencity:	0.248
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.865

Download Data

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

Natural Product: NPC11147

Natural Product ID:	NPC11147
*Common Name:**	Septicine
IUPAC Name:	(8aR)-6,7-bis(3,4-dimethoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizine
Synonyms:	Septicine
Standard InCHIKey:	MXMHNOVMTJDCLE-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C24H29NO4/c1-26-21-9-7-16(12-23(21)28-3)19-14-18-6-5-11-25(18)15-20(19)17-8-10-22(27-2)24(13-17)29-4/h7-10,12-13,18H,5-6,11,14-15H2,1-4H3/t18-/m1/s1
SMILES:	COc1ccc(cc1OC)C1=C(C[C@@H]2N(C1)CCC2)c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1092163
PubChem CID:	10763252
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
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	Stems	Tainan Hsien, Taiwan, Republic of China	2000-JAN	PMID[16038551]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19938815]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6257	Ficus septica	Species	Moraceae	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
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	38000.0	nM	PMID[461147]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	63000.0	nM	PMID[461147]

☑ 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 NPC11147 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	274
0.1-0.2	1461
0.2-0.3	7973
0.3-0.4	10047
0.4-0.5	6971
0.5-0.6	11657
0.6-0.7	3308
0.7-0.8	889
0.8-0.85	89
0.85-0.9	23
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9764	High Similarity	NPC118419
0.9394	High Similarity	NPC193528
0.9098	High Similarity	NPC475828
0.8905	High Similarity	NPC474915
0.8905	High Similarity	NPC328750
0.8905	High Similarity	NPC188163
0.8905	High Similarity	NPC213206
0.8855	High Similarity	NPC172403
0.8832	High Similarity	NPC314682
0.8732	High Similarity	NPC475959
0.8671	High Similarity	NPC219162
0.8643	High Similarity	NPC476567
0.8643	High Similarity	NPC136860
0.8643	High Similarity	NPC128019
0.8613	High Similarity	NPC231884
0.8613	High Similarity	NPC167944
0.8613	High Similarity	NPC42793
0.8601	High Similarity	NPC130941
0.8531	High Similarity	NPC106295
0.8531	High Similarity	NPC95075
0.8531	High Similarity	NPC90844
0.8531	High Similarity	NPC210437
0.8531	High Similarity	NPC51957
0.8531	High Similarity	NPC476144
0.8531	High Similarity	NPC16107
0.8531	High Similarity	NPC253883
0.8521	High Similarity	NPC185838
0.8472	Intermediate Similarity	NPC428
0.8472	Intermediate Similarity	NPC476571
0.8472	Intermediate Similarity	NPC7467
0.8472	Intermediate Similarity	NPC24233
0.8472	Intermediate Similarity	NPC147390
0.8472	Intermediate Similarity	NPC246587
0.8472	Intermediate Similarity	NPC135538
0.8425	Intermediate Similarity	NPC476568
0.8403	Intermediate Similarity	NPC321505
0.8403	Intermediate Similarity	NPC179825
0.8403	Intermediate Similarity	NPC191376
0.8403	Intermediate Similarity	NPC476151
0.8378	Intermediate Similarity	NPC138487
0.8378	Intermediate Similarity	NPC244112
0.8378	Intermediate Similarity	NPC216459
0.8378	Intermediate Similarity	NPC41178
0.8378	Intermediate Similarity	NPC93593
0.8367	Intermediate Similarity	NPC233029
0.8367	Intermediate Similarity	NPC210148
0.8333	Intermediate Similarity	NPC298486
0.8322	Intermediate Similarity	NPC146288
0.8309	Intermediate Similarity	NPC160193
0.8288	Intermediate Similarity	NPC103379
0.8288	Intermediate Similarity	NPC477565
0.8288	Intermediate Similarity	NPC92541
0.8288	Intermediate Similarity	NPC44869
0.8264	Intermediate Similarity	NPC130926
0.8264	Intermediate Similarity	NPC145304
0.8243	Intermediate Similarity	NPC26601
0.8239	Intermediate Similarity	NPC323204
0.8231	Intermediate Similarity	NPC192768
0.8231	Intermediate Similarity	NPC220858
0.8231	Intermediate Similarity	NPC97221
0.8231	Intermediate Similarity	NPC151895
0.8231	Intermediate Similarity	NPC88249
0.8222	Intermediate Similarity	NPC301713
0.82	Intermediate Similarity	NPC234392
0.82	Intermediate Similarity	NPC31311
0.82	Intermediate Similarity	NPC186063
0.8176	Intermediate Similarity	NPC81733
0.8176	Intermediate Similarity	NPC326316
0.817	Intermediate Similarity	NPC233650
0.8163	Intermediate Similarity	NPC207824
0.8163	Intermediate Similarity	NPC60538
0.8163	Intermediate Similarity	NPC211296
0.8151	Intermediate Similarity	NPC144863
0.8133	Intermediate Similarity	NPC54379
0.8133	Intermediate Similarity	NPC127674
0.8133	Intermediate Similarity	NPC39701
0.8133	Intermediate Similarity	NPC207757
0.8133	Intermediate Similarity	NPC172765
0.8133	Intermediate Similarity	NPC184026
0.8133	Intermediate Similarity	NPC189266
0.8133	Intermediate Similarity	NPC276588
0.8133	Intermediate Similarity	NPC278799
0.8133	Intermediate Similarity	NPC2413
0.8133	Intermediate Similarity	NPC76079
0.8133	Intermediate Similarity	NPC204828
0.8133	Intermediate Similarity	NPC249797
0.8133	Intermediate Similarity	NPC78733
0.8133	Intermediate Similarity	NPC5238
0.8133	Intermediate Similarity	NPC110416
0.8133	Intermediate Similarity	NPC295691
0.8133	Intermediate Similarity	NPC469817
0.8133	Intermediate Similarity	NPC193949
0.8117	Intermediate Similarity	NPC134858
0.8116	Intermediate Similarity	NPC476570
0.8092	Intermediate Similarity	NPC111485
0.8092	Intermediate Similarity	NPC216816
0.8085	Intermediate Similarity	NPC7018
0.8079	Intermediate Similarity	NPC323443
0.8079	Intermediate Similarity	NPC477132
0.8079	Intermediate Similarity	NPC25084
0.8079	Intermediate Similarity	NPC247639
0.8079	Intermediate Similarity	NPC477133
0.8079	Intermediate Similarity	NPC180756
0.8079	Intermediate Similarity	NPC147091
0.8058	Intermediate Similarity	NPC214869
0.8054	Intermediate Similarity	NPC76213
0.8054	Intermediate Similarity	NPC8337
0.8054	Intermediate Similarity	NPC85747
0.8054	Intermediate Similarity	NPC277669
0.8039	Intermediate Similarity	NPC477559
0.8039	Intermediate Similarity	NPC306902
0.8039	Intermediate Similarity	NPC232924
0.8039	Intermediate Similarity	NPC266753
0.8039	Intermediate Similarity	NPC160298
0.8028	Intermediate Similarity	NPC253429
0.8026	Intermediate Similarity	NPC476572
0.8015	Intermediate Similarity	NPC120075
0.8013	Intermediate Similarity	NPC80129
0.8013	Intermediate Similarity	NPC150879
0.8013	Intermediate Similarity	NPC187022
0.8013	Intermediate Similarity	NPC325871
0.8013	Intermediate Similarity	NPC210140
0.8013	Intermediate Similarity	NPC99659
0.8	Intermediate Similarity	NPC238530
0.8	Intermediate Similarity	NPC276944
0.8	Intermediate Similarity	NPC148898
0.8	Intermediate Similarity	NPC232514
0.8	Intermediate Similarity	NPC47194
0.7987	Intermediate Similarity	NPC274026
0.7986	Intermediate Similarity	NPC114102
0.7984	Intermediate Similarity	NPC165106
0.7974	Intermediate Similarity	NPC477080
0.7949	Intermediate Similarity	NPC476432
0.7949	Intermediate Similarity	NPC24264
0.7947	Intermediate Similarity	NPC477564
0.7947	Intermediate Similarity	NPC2295
0.7933	Intermediate Similarity	NPC476579
0.7922	Intermediate Similarity	NPC4304
0.7922	Intermediate Similarity	NPC205167
0.7914	Intermediate Similarity	NPC52029
0.7914	Intermediate Similarity	NPC195749
0.7914	Intermediate Similarity	NPC35961
0.7902	Intermediate Similarity	NPC248505
0.7902	Intermediate Similarity	NPC95366
0.7902	Intermediate Similarity	NPC252107
0.7898	Intermediate Similarity	NPC247389
0.7885	Intermediate Similarity	NPC167546
0.7885	Intermediate Similarity	NPC302527
0.7885	Intermediate Similarity	NPC76116
0.7885	Intermediate Similarity	NPC225774
0.7885	Intermediate Similarity	NPC16805
0.7881	Intermediate Similarity	NPC133011
0.7881	Intermediate Similarity	NPC82285
0.7881	Intermediate Similarity	NPC476580
0.7872	Intermediate Similarity	NPC160692
0.7867	Intermediate Similarity	NPC223125
0.7867	Intermediate Similarity	NPC13397
0.7863	Intermediate Similarity	NPC473264
0.7863	Intermediate Similarity	NPC475815
0.7862	Intermediate Similarity	NPC470925
0.7852	Intermediate Similarity	NPC211992
0.7847	Intermediate Similarity	NPC210086
0.7843	Intermediate Similarity	NPC126519
0.7843	Intermediate Similarity	NPC203784
0.7843	Intermediate Similarity	NPC170503
0.7842	Intermediate Similarity	NPC155838
0.7838	Intermediate Similarity	NPC473934
0.7836	Intermediate Similarity	NPC344161
0.7836	Intermediate Similarity	NPC321133
0.7834	Intermediate Similarity	NPC219341
0.7832	Intermediate Similarity	NPC145446
0.7832	Intermediate Similarity	NPC131204
0.7832	Intermediate Similarity	NPC301050
0.7832	Intermediate Similarity	NPC99078
0.7832	Intermediate Similarity	NPC137172
0.7832	Intermediate Similarity	NPC416184
0.7821	Intermediate Similarity	NPC475393
0.7821	Intermediate Similarity	NPC218614
0.7806	Intermediate Similarity	NPC97072
0.7806	Intermediate Similarity	NPC27410
0.7806	Intermediate Similarity	NPC249274
0.7806	Intermediate Similarity	NPC215829
0.7806	Intermediate Similarity	NPC166014
0.7803	Intermediate Similarity	NPC9341
0.7803	Intermediate Similarity	NPC81067
0.7786	Intermediate Similarity	NPC470706
0.7786	Intermediate Similarity	NPC262641
0.7785	Intermediate Similarity	NPC298979
0.7785	Intermediate Similarity	NPC210918
0.7778	Intermediate Similarity	NPC470707
0.7778	Intermediate Similarity	NPC220923
0.7771	Intermediate Similarity	NPC180306
0.777	Intermediate Similarity	NPC153990
0.777	Intermediate Similarity	NPC251571
0.7763	Intermediate Similarity	NPC223124
0.7762	Intermediate Similarity	NPC136330
0.7762	Intermediate Similarity	NPC230698
0.7762	Intermediate Similarity	NPC277042
0.7762	Intermediate Similarity	NPC196609
0.7762	Intermediate Similarity	NPC205178

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 NPC11147 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	691
0.2-0.3	958
0.3-0.4	1987
0.4-0.5	2731
0.5-0.6	1681
0.6-0.7	743
0.7-0.8	166
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8905	High Similarity	NPD4664	Clinical (unspecified phase)
0.8797	High Similarity	NPD5718	Phase 2
0.8788	High Similarity	NPD5752	Clinical (unspecified phase)
0.8613	High Similarity	NPD6895	Approved
0.8613	High Similarity	NPD6896	Approved
0.8582	High Similarity	NPD2669	Clinical (unspecified phase)
0.8531	High Similarity	NPD4584	Approved
0.8451	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD5241	Discontinued
0.831	Intermediate Similarity	NPD4237	Approved
0.831	Intermediate Similarity	NPD4236	Phase 3
0.8264	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4017	Approved
0.8138	Intermediate Similarity	NPD7124	Phase 2
0.8125	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4162	Approved
0.8056	Intermediate Similarity	NPD3060	Approved
0.8041	Intermediate Similarity	NPD6031	Approved
0.8041	Intermediate Similarity	NPD6030	Approved
0.8013	Intermediate Similarity	NPD7298	Approved
0.8	Intermediate Similarity	NPD6331	Phase 2
0.7984	Intermediate Similarity	NPD5283	Phase 1
0.7961	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7905	Discontinued
0.7945	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3640	Phase 3
0.7919	Intermediate Similarity	NPD3641	Approved
0.7919	Intermediate Similarity	NPD3639	Approved
0.7867	Intermediate Similarity	NPD4210	Discontinued
0.7857	Intermediate Similarity	NPD6788	Approved
0.7843	Intermediate Similarity	NPD2977	Approved
0.7843	Intermediate Similarity	NPD2978	Approved
0.7836	Intermediate Similarity	NPD2668	Approved
0.7836	Intermediate Similarity	NPD2667	Approved
0.7815	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD5177	Phase 3
0.78	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD2492	Phase 1
0.7762	Intermediate Similarity	NPD2653	Approved
0.7746	Intermediate Similarity	NPD3110	Approved
0.7746	Intermediate Similarity	NPD3109	Approved
0.7727	Intermediate Similarity	NPD5773	Approved
0.7727	Intermediate Similarity	NPD5772	Approved
0.7712	Intermediate Similarity	NPD4773	Phase 2
0.7712	Intermediate Similarity	NPD7110	Phase 1
0.7712	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD4772	Phase 2
0.7707	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7018	Phase 2
0.7697	Intermediate Similarity	NPD4005	Discontinued
0.7692	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7831	Phase 2
0.7692	Intermediate Similarity	NPD7833	Phase 2
0.7688	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2674	Phase 3
0.7667	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6875	Approved
0.7647	Intermediate Similarity	NPD6876	Approved
0.7635	Intermediate Similarity	NPD5754	Discontinued
0.7626	Intermediate Similarity	NPD3053	Approved
0.7626	Intermediate Similarity	NPD4098	Discontinued
0.7626	Intermediate Similarity	NPD3055	Approved
0.7625	Intermediate Similarity	NPD4481	Phase 3
0.7616	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4010	Discontinued
0.761	Intermediate Similarity	NPD3051	Approved
0.761	Intermediate Similarity	NPD4166	Phase 2
0.7597	Intermediate Similarity	NPD6386	Approved
0.7597	Intermediate Similarity	NPD6385	Approved
0.7586	Intermediate Similarity	NPD6111	Discontinued
0.7566	Intermediate Similarity	NPD5976	Discontinued
0.7564	Intermediate Similarity	NPD2560	Approved
0.7564	Intermediate Similarity	NPD2563	Approved
0.7564	Intermediate Similarity	NPD5977	Approved
0.7564	Intermediate Similarity	NPD5978	Approved
0.7562	Intermediate Similarity	NPD2970	Approved
0.7562	Intermediate Similarity	NPD2969	Approved
0.7554	Intermediate Similarity	NPD2922	Phase 1
0.7552	Intermediate Similarity	NPD3532	Approved
0.7552	Intermediate Similarity	NPD3530	Approved
0.7552	Intermediate Similarity	NPD4475	Approved
0.7552	Intermediate Similarity	NPD4474	Approved
0.7552	Intermediate Similarity	NPD3531	Approved
0.755	Intermediate Similarity	NPD4123	Phase 3
0.7547	Intermediate Similarity	NPD7802	Discontinued
0.7537	Intermediate Similarity	NPD3596	Phase 2
0.7536	Intermediate Similarity	NPD2230	Approved
0.7536	Intermediate Similarity	NPD2233	Approved
0.7536	Intermediate Similarity	NPD2232	Approved
0.7531	Intermediate Similarity	NPD8099	Discontinued
0.7531	Intermediate Similarity	NPD8251	Approved
0.7531	Intermediate Similarity	NPD8252	Approved
0.7517	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD27	Approved
0.7516	Intermediate Similarity	NPD2489	Approved
0.75	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8156	Discontinued
0.7484	Intermediate Similarity	NPD6873	Phase 2
0.7483	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3124	Discontinued
0.7483	Intermediate Similarity	NPD5297	Approved
0.7483	Intermediate Similarity	NPD2161	Phase 2
0.7483	Intermediate Similarity	NPD5109	Approved
0.7483	Intermediate Similarity	NPD5110	Phase 2
0.7483	Intermediate Similarity	NPD3145	Approved
0.7483	Intermediate Similarity	NPD5111	Phase 2
0.7483	Intermediate Similarity	NPD3144	Approved
0.7482	Intermediate Similarity	NPD1669	Approved
0.747	Intermediate Similarity	NPD7281	Phase 3
0.747	Intermediate Similarity	NPD7280	Phase 3
0.7447	Intermediate Similarity	NPD6584	Phase 3
0.7438	Intermediate Similarity	NPD6107	Approved
0.7436	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1424	Approved
0.7434	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1375	Discontinued
0.7426	Intermediate Similarity	NPD6581	Approved
0.7426	Intermediate Similarity	NPD2486	Discontinued
0.7426	Intermediate Similarity	NPD6580	Approved
0.7407	Intermediate Similarity	NPD2898	Approved
0.7391	Intermediate Similarity	NPD6071	Discontinued
0.7391	Intermediate Similarity	NPD3294	Phase 2
0.7383	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7037	Approved
0.7379	Intermediate Similarity	NPD2238	Phase 2
0.7372	Intermediate Similarity	NPD2595	Approved
0.7372	Intermediate Similarity	NPD6382	Discontinued
0.7372	Intermediate Similarity	NPD2594	Approved
0.7372	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1420	Approved
0.7357	Intermediate Similarity	NPD1421	Approved
0.7355	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5536	Phase 2
0.7325	Intermediate Similarity	NPD5720	Discontinued
0.732	Intermediate Similarity	NPD2874	Phase 2
0.732	Intermediate Similarity	NPD7019	Approved
0.732	Intermediate Similarity	NPD7020	Approved
0.7317	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4675	Approved
0.7308	Intermediate Similarity	NPD4678	Approved
0.7305	Intermediate Similarity	NPD5310	Approved
0.7305	Intermediate Similarity	NPD5311	Approved
0.7293	Intermediate Similarity	NPD4572	Approved
0.7293	Intermediate Similarity	NPD4571	Approved
0.7293	Intermediate Similarity	NPD4573	Approved
0.7292	Intermediate Similarity	NPD5746	Approved
0.7289	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6297	Approved
0.7285	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2986	Phase 2
0.7279	Intermediate Similarity	NPD2989	Phase 2
0.7273	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5677	Discontinued
0.7267	Intermediate Similarity	NPD7153	Discontinued
0.7259	Intermediate Similarity	NPD595	Approved
0.7259	Intermediate Similarity	NPD593	Approved
0.725	Intermediate Similarity	NPD5604	Discontinued
0.725	Intermediate Similarity	NPD4055	Discovery
0.7246	Intermediate Similarity	NPD3445	Approved
0.7246	Intermediate Similarity	NPD4093	Discontinued
0.7246	Intermediate Similarity	NPD3443	Approved
0.7246	Intermediate Similarity	NPD3444	Approved
0.7239	Intermediate Similarity	NPD6687	Approved
0.7239	Intermediate Similarity	NPD6688	Approved
0.7234	Intermediate Similarity	NPD6543	Approved
0.7234	Intermediate Similarity	NPD6582	Phase 2
0.7234	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6540	Phase 3
0.7234	Intermediate Similarity	NPD6583	Phase 3
0.7234	Intermediate Similarity	NPD6542	Approved
0.7234	Intermediate Similarity	NPD6539	Approved
0.7226	Intermediate Similarity	NPD2122	Discontinued
0.7219	Intermediate Similarity	NPD8053	Approved
0.7219	Intermediate Similarity	NPD8054	Approved
0.7208	Intermediate Similarity	NPD4739	Approved
0.7206	Intermediate Similarity	NPD2557	Approved
0.7205	Intermediate Similarity	NPD7400	Phase 3
0.7203	Intermediate Similarity	NPD2990	Approved
0.7203	Intermediate Similarity	NPD2987	Approved
0.7202	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2376	Approved
0.72	Intermediate Similarity	NPD2377	Approved
0.72	Intermediate Similarity	NPD2378	Approved
0.7197	Intermediate Similarity	NPD4179	Approved
0.7197	Intermediate Similarity	NPD4180	Approved
0.7193	Intermediate Similarity	NPD7906	Approved
0.7193	Intermediate Similarity	NPD7291	Discontinued
0.7192	Intermediate Similarity	NPD5745	Approved
0.7192	Intermediate Similarity	NPD2245	Discovery
0.719	Intermediate Similarity	NPD6667	Approved
0.719	Intermediate Similarity	NPD6666	Approved
0.7188	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1753	Discontinued
0.7179	Intermediate Similarity	NPD3687	Approved
0.7179	Intermediate Similarity	NPD3686	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