NPASS Compound

Structure

CID76116 OpenBabel06191715412D 29 33 0 0 1 0 0 0 0 0999 V2000 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 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 3.4641 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 -0.0000 2.0000 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 0.0000 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 2.5981 1.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 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 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 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 -0.4593 2.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 24 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 22 2 0 0 0 0 19 5 1 6 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 23 25 1 1 0 0 0 24 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	395.17
Volume:	400.075
LogP:	2.352
LogD:	2.051
LogS:	-2.57
# Rotatable Bonds:	3
TPSA:	70.98
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	3.988
Fsp3:	0.391
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:	-5.689
MDCK Permeability:	2.6368843464297242e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.923
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.607
Plasma Protein Binding (PPB):	78.85579681396484%
Volume Distribution (VD):	1.975
Pgp-substrate:	16.8364200592041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.11
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.832
CYP2D6-inhibitor:	0.111
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.844

ADMET: Excretion

Clearance (CL):	9.963
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.653
Rat Oral Acute Toxicity:	0.717
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.884
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC76116

Natural Product ID:	NPC76116
*Common Name:**	Tylophoridicine F
IUPAC Name:	(13aS,14R)-3,6,7-trimethoxy-10-oxido-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-10-ium-14-ol
Synonyms:	Tylophoridicine F
Standard InCHIKey:	SHQULSXBVKOENG-OSAZCDQKSA-N
Standard InCHI:	InChI=1S/C23H25NO5/c1-27-13-6-7-14-15(9-13)16-10-20(28-2)21(29-3)11-17(16)18-12-24(26)8-4-5-19(24)23(25)22(14)18/h6-7,9-11,19,23,25H,4-5,8,12H2,1-3H3/t19-,23-,24?/m0/s1
SMILES:	COc1ccc2c(c1)c1cc(c(cc1c1CN3(=O)CCC[C@H]3[C@@H](c21)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401479
PubChem CID:	44443383
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0001906] Phenanthroindolizidines

*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
NPO18435	Tylophora atrofolliculata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18435	Tylophora atrofolliculata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18435	Tylophora atrofolliculata	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
GI50	2
IC50	3

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	GI50	=	71.0	nM	PMID[489539]
NPT461	Cell Line	PANC-1	Homo sapiens	GI50	=	63.0	nM	PMID[489539]
NPT2	Others	Unspecified		IC50	=	367.0	nM	PMID[489539]
NPT2	Others	Unspecified		IC50	>	1000.0	nM	PMID[489539]
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	IC50	>	3000.0	nM	PMID[489539]

☑ 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 NPC76116 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	284
0.1-0.2	1401
0.2-0.3	5436
0.3-0.4	12261
0.4-0.5	6273
0.5-0.6	12774
0.6-0.7	3479
0.7-0.8	590
0.8-0.85	174
0.85-0.9	12
0.9-0.95	5
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC160570
0.9806	High Similarity	NPC164429
0.9618	High Similarity	NPC329911
0.9211	High Similarity	NPC44869
0.8981	High Similarity	NPC477133
0.8981	High Similarity	NPC477132
0.8938	High Similarity	NPC233650
0.8882	High Similarity	NPC134858
0.8773	High Similarity	NPC150879
0.8773	High Similarity	NPC210140
0.8588	High Similarity	NPC233718
0.8457	Intermediate Similarity	NPC475326
0.8438	Intermediate Similarity	NPC470924
0.8438	Intermediate Similarity	NPC37272
0.8355	Intermediate Similarity	NPC475828
0.8323	Intermediate Similarity	NPC26601
0.8313	Intermediate Similarity	NPC169743
0.8312	Intermediate Similarity	NPC210086
0.8282	Intermediate Similarity	NPC147091
0.8282	Intermediate Similarity	NPC186063
0.825	Intermediate Similarity	NPC219162
0.8242	Intermediate Similarity	NPC205167
0.8199	Intermediate Similarity	NPC274026
0.8187	Intermediate Similarity	NPC130941
0.8182	Intermediate Similarity	NPC59028
0.8182	Intermediate Similarity	NPC92191
0.8133	Intermediate Similarity	NPC249274
0.8125	Intermediate Similarity	NPC90844
0.8125	Intermediate Similarity	NPC253883
0.8125	Intermediate Similarity	NPC95075
0.807	Intermediate Similarity	NPC477640
0.807	Intermediate Similarity	NPC470739
0.807	Intermediate Similarity	NPC225597
0.8059	Intermediate Similarity	NPC266176
0.8059	Intermediate Similarity	NPC290759
0.8059	Intermediate Similarity	NPC475686
0.8059	Intermediate Similarity	NPC158148
0.8059	Intermediate Similarity	NPC82533
0.8059	Intermediate Similarity	NPC58766
0.8057	Intermediate Similarity	NPC248642
0.8046	Intermediate Similarity	NPC126284
0.8024	Intermediate Similarity	NPC215829
0.8024	Intermediate Similarity	NPC97072
0.8012	Intermediate Similarity	NPC474475
0.8011	Intermediate Similarity	NPC156576
0.8	Intermediate Similarity	NPC244112
0.8	Intermediate Similarity	NPC185838
0.7989	Intermediate Similarity	NPC477560
0.7988	Intermediate Similarity	NPC82285
0.7988	Intermediate Similarity	NPC133011
0.7963	Intermediate Similarity	NPC476571
0.7963	Intermediate Similarity	NPC135538
0.7963	Intermediate Similarity	NPC24233
0.7963	Intermediate Similarity	NPC147390
0.7963	Intermediate Similarity	NPC428
0.7963	Intermediate Similarity	NPC246587
0.7919	Intermediate Similarity	NPC2314
0.7917	Intermediate Similarity	NPC27410
0.7917	Intermediate Similarity	NPC166014
0.7914	Intermediate Similarity	NPC92541
0.7901	Intermediate Similarity	NPC476151
0.7901	Intermediate Similarity	NPC191376
0.7901	Intermediate Similarity	NPC179825
0.7901	Intermediate Similarity	NPC321505
0.7898	Intermediate Similarity	NPC193528
0.7895	Intermediate Similarity	NPC298979
0.7895	Intermediate Similarity	NPC100566
0.7895	Intermediate Similarity	NPC181653
0.7895	Intermediate Similarity	NPC190332
0.7888	Intermediate Similarity	NPC130926
0.7885	Intermediate Similarity	NPC11147
0.787	Intermediate Similarity	NPC60186
0.7866	Intermediate Similarity	NPC88249
0.7866	Intermediate Similarity	NPC97221
0.7866	Intermediate Similarity	NPC192768
0.7866	Intermediate Similarity	NPC151895
0.7866	Intermediate Similarity	NPC220858
0.7862	Intermediate Similarity	NPC213206
0.7862	Intermediate Similarity	NPC188163
0.7862	Intermediate Similarity	NPC474915
0.7862	Intermediate Similarity	NPC328750
0.7829	Intermediate Similarity	NPC474470
0.7824	Intermediate Similarity	NPC320104
0.7824	Intermediate Similarity	NPC324144
0.7821	Intermediate Similarity	NPC214116
0.7818	Intermediate Similarity	NPC81733
0.7818	Intermediate Similarity	NPC326316
0.7811	Intermediate Similarity	NPC4304
0.7805	Intermediate Similarity	NPC477565
0.7805	Intermediate Similarity	NPC103379
0.7799	Intermediate Similarity	NPC314682
0.7798	Intermediate Similarity	NPC40389
0.7798	Intermediate Similarity	NPC78359
0.7798	Intermediate Similarity	NPC148014
0.7798	Intermediate Similarity	NPC315707
0.7798	Intermediate Similarity	NPC65490
0.7791	Intermediate Similarity	NPC306555
0.7791	Intermediate Similarity	NPC158376
0.7791	Intermediate Similarity	NPC145832
0.7791	Intermediate Similarity	NPC117188
0.7791	Intermediate Similarity	NPC144863
0.7791	Intermediate Similarity	NPC205421
0.7791	Intermediate Similarity	NPC474931
0.7791	Intermediate Similarity	NPC81218
0.7791	Intermediate Similarity	NPC12053
0.7784	Intermediate Similarity	NPC249797
0.7784	Intermediate Similarity	NPC110416
0.7784	Intermediate Similarity	NPC469817
0.7784	Intermediate Similarity	NPC207757
0.7784	Intermediate Similarity	NPC295691
0.7784	Intermediate Similarity	NPC193949
0.7784	Intermediate Similarity	NPC39701
0.7784	Intermediate Similarity	NPC278799
0.7784	Intermediate Similarity	NPC204828
0.7784	Intermediate Similarity	NPC78733
0.7784	Intermediate Similarity	NPC127674
0.7784	Intermediate Similarity	NPC76079
0.7784	Intermediate Similarity	NPC276588
0.7784	Intermediate Similarity	NPC54379
0.7784	Intermediate Similarity	NPC172765
0.7784	Intermediate Similarity	NPC189266
0.7784	Intermediate Similarity	NPC5238
0.7784	Intermediate Similarity	NPC2413
0.7784	Intermediate Similarity	NPC184026
0.7778	Intermediate Similarity	NPC253043
0.7778	Intermediate Similarity	NPC212794
0.7778	Intermediate Similarity	NPC136508
0.7778	Intermediate Similarity	NPC477563
0.7778	Intermediate Similarity	NPC306843
0.7778	Intermediate Similarity	NPC78222
0.7778	Intermediate Similarity	NPC196447
0.7778	Intermediate Similarity	NPC13504
0.7778	Intermediate Similarity	NPC96603
0.7764	Intermediate Similarity	NPC128019
0.7764	Intermediate Similarity	NPC136860
0.7764	Intermediate Similarity	NPC476567
0.7759	Intermediate Similarity	NPC57272
0.7751	Intermediate Similarity	NPC111485
0.7751	Intermediate Similarity	NPC477080
0.7744	Intermediate Similarity	NPC475959
0.774	Intermediate Similarity	NPC244554
0.7738	Intermediate Similarity	NPC37205
0.7738	Intermediate Similarity	NPC160931
0.7733	Intermediate Similarity	NPC476002
0.7727	Intermediate Similarity	NPC237044
0.7706	Intermediate Similarity	NPC306902
0.7706	Intermediate Similarity	NPC232924
0.7706	Intermediate Similarity	NPC160298
0.7706	Intermediate Similarity	NPC477559
0.7706	Intermediate Similarity	NPC18402
0.7706	Intermediate Similarity	NPC266753
0.7697	Intermediate Similarity	NPC207824
0.7697	Intermediate Similarity	NPC60538
0.7692	Intermediate Similarity	NPC118419
0.7692	Intermediate Similarity	NPC476572
0.7688	Intermediate Similarity	NPC252960
0.7688	Intermediate Similarity	NPC301189
0.7688	Intermediate Similarity	NPC298186
0.7684	Intermediate Similarity	NPC114364
0.7684	Intermediate Similarity	NPC320223
0.7684	Intermediate Similarity	NPC474325
0.7684	Intermediate Similarity	NPC294790
0.7684	Intermediate Similarity	NPC148693
0.7684	Intermediate Similarity	NPC118633
0.7683	Intermediate Similarity	NPC51957
0.7683	Intermediate Similarity	NPC16107
0.7683	Intermediate Similarity	NPC210437
0.7683	Intermediate Similarity	NPC476144
0.7683	Intermediate Similarity	NPC106295
0.7679	Intermediate Similarity	NPC325871
0.7679	Intermediate Similarity	NPC99659
0.7674	Intermediate Similarity	NPC238530
0.7674	Intermediate Similarity	NPC276944
0.7674	Intermediate Similarity	NPC232514
0.7674	Intermediate Similarity	NPC247972
0.767	Intermediate Similarity	NPC128560
0.767	Intermediate Similarity	NPC229166
0.767	Intermediate Similarity	NPC304675
0.767	Intermediate Similarity	NPC199465
0.7665	Intermediate Similarity	NPC148898
0.7657	Intermediate Similarity	NPC476331
0.7654	Intermediate Similarity	NPC476575
0.764	Intermediate Similarity	NPC474745
0.7636	Intermediate Similarity	NPC7467
0.763	Intermediate Similarity	NPC35627
0.763	Intermediate Similarity	NPC81247
0.763	Intermediate Similarity	NPC124657
0.763	Intermediate Similarity	NPC476573
0.763	Intermediate Similarity	NPC476432
0.763	Intermediate Similarity	NPC24264
0.7627	Intermediate Similarity	NPC241704
0.7616	Intermediate Similarity	NPC1229
0.7616	Intermediate Similarity	NPC218614
0.761	Intermediate Similarity	NPC131204
0.761	Intermediate Similarity	NPC301050
0.7605	Intermediate Similarity	NPC476568
0.7605	Intermediate Similarity	NPC76213
0.7605	Intermediate Similarity	NPC277669
0.7588	Intermediate Similarity	NPC129603
0.7586	Intermediate Similarity	NPC247389

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 NPC76116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	660
0.2-0.3	912
0.3-0.4	1950
0.4-0.5	2652
0.5-0.6	1907
0.6-0.7	741
0.7-0.8	144
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7937	Intermediate Similarity	NPD5241	Discontinued
0.7862	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD2563	Approved
0.7798	Intermediate Similarity	NPD2560	Approved
0.7738	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD4773	Phase 2
0.7725	Intermediate Similarity	NPD4772	Phase 2
0.7719	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7831	Phase 2
0.7706	Intermediate Similarity	NPD7833	Phase 2
0.7706	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2969	Approved
0.7688	Intermediate Similarity	NPD2970	Approved
0.7683	Intermediate Similarity	NPD4584	Approved
0.7644	Intermediate Similarity	NPD27	Approved
0.7644	Intermediate Similarity	NPD2489	Approved
0.763	Intermediate Similarity	NPD6071	Discontinued
0.7593	Intermediate Similarity	NPD4236	Phase 3
0.7593	Intermediate Similarity	NPD4237	Approved
0.7544	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD2898	Approved
0.7529	Intermediate Similarity	NPD3051	Approved
0.7403	Intermediate Similarity	NPD7313	Approved
0.7403	Intermediate Similarity	NPD7310	Approved
0.7403	Intermediate Similarity	NPD7312	Approved
0.7403	Intermediate Similarity	NPD7311	Approved
0.7378	Intermediate Similarity	NPD3060	Approved
0.7363	Intermediate Similarity	NPD7309	Approved
0.7342	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7906	Approved
0.7294	Intermediate Similarity	NPD4017	Approved
0.7283	Intermediate Similarity	NPD4663	Approved
0.7278	Intermediate Similarity	NPD6031	Approved
0.7278	Intermediate Similarity	NPD3639	Approved
0.7278	Intermediate Similarity	NPD3641	Approved
0.7278	Intermediate Similarity	NPD3640	Phase 3
0.7278	Intermediate Similarity	NPD6030	Approved
0.7267	Intermediate Similarity	NPD7298	Approved
0.7262	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7400	Phase 3
0.7247	Intermediate Similarity	NPD4481	Phase 3
0.7246	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4010	Discontinued
0.7229	Intermediate Similarity	NPD6331	Phase 2
0.7225	Intermediate Similarity	NPD5772	Approved
0.7225	Intermediate Similarity	NPD2977	Approved
0.7225	Intermediate Similarity	NPD2978	Approved
0.7225	Intermediate Similarity	NPD5773	Approved
0.7219	Intermediate Similarity	NPD6090	Discontinued
0.7213	Intermediate Similarity	NPD4577	Approved
0.7213	Intermediate Similarity	NPD4578	Approved
0.7212	Intermediate Similarity	NPD7037	Approved
0.7202	Intermediate Similarity	NPD2421	Approved
0.7202	Intermediate Similarity	NPD2420	Approved
0.7186	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6107	Approved
0.7169	Intermediate Similarity	NPD4162	Approved
0.7093	Intermediate Similarity	NPD4005	Discontinued
0.7083	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5177	Phase 3
0.7063	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5709	Phase 3
0.7049	Intermediate Similarity	NPD6297	Approved
0.7041	Intermediate Similarity	NPD3845	Phase 1
0.7039	Intermediate Similarity	NPD4166	Phase 2
0.7037	Intermediate Similarity	NPD2674	Phase 3
0.7035	Intermediate Similarity	NPD4210	Discontinued
0.703	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD4666	Phase 3
0.7017	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6688	Approved
0.7	Intermediate Similarity	NPD6687	Approved
0.6989	Remote Similarity	NPD8053	Approved
0.6989	Remote Similarity	NPD6853	Approved
0.6989	Remote Similarity	NPD8054	Approved
0.6989	Remote Similarity	NPD6851	Approved
0.6975	Remote Similarity	NPD5718	Phase 2
0.6974	Remote Similarity	NPD3533	Approved
0.6974	Remote Similarity	NPD2491	Approved
0.6974	Remote Similarity	NPD2972	Approved
0.6974	Remote Similarity	NPD3448	Approved
0.6973	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6896	Approved
0.697	Remote Similarity	NPD6895	Approved
0.6959	Remote Similarity	NPD4123	Phase 3
0.695	Remote Similarity	NPD5676	Approved
0.694	Remote Similarity	NPD8156	Discontinued
0.6928	Remote Similarity	NPD1753	Discontinued
0.6927	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3124	Discontinued
0.6895	Remote Similarity	NPD2490	Approved
0.6895	Remote Similarity	NPD2488	Approved
0.6895	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2973	Approved
0.6891	Remote Similarity	NPD2975	Approved
0.6891	Remote Similarity	NPD2974	Approved
0.689	Remote Similarity	NPD3110	Approved
0.689	Remote Similarity	NPD3109	Approved
0.689	Remote Similarity	NPD2238	Phase 2
0.6889	Remote Similarity	NPD7802	Discontinued
0.6888	Remote Similarity	NPD3057	Approved
0.6886	Remote Similarity	NPD2161	Phase 2
0.6885	Remote Similarity	NPD8252	Approved
0.6885	Remote Similarity	NPD8251	Approved
0.6885	Remote Similarity	NPD8099	Discontinued
0.6882	Remote Similarity	NPD3692	Discontinued
0.6879	Remote Similarity	NPD5976	Discontinued
0.6878	Remote Similarity	NPD3398	Discontinued
0.6871	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3145	Approved
0.6871	Remote Similarity	NPD3144	Approved
0.6854	Remote Similarity	NPD6788	Approved
0.6848	Remote Similarity	NPD5313	Approved
0.6848	Remote Similarity	NPD5312	Approved
0.6845	Remote Similarity	NPD7281	Phase 3
0.6845	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7280	Phase 3
0.6839	Remote Similarity	NPD3687	Approved
0.6839	Remote Similarity	NPD3686	Approved
0.6839	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3450	Approved
0.6837	Remote Similarity	NPD3452	Approved
0.6837	Remote Similarity	NPD2494	Approved
0.6837	Remote Similarity	NPD2493	Approved
0.6829	Remote Similarity	NPD4474	Approved
0.6829	Remote Similarity	NPD4475	Approved
0.6821	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2388	Discontinued
0.6805	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7153	Discontinued
0.68	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4859	Phase 1
0.68	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7291	Discontinued
0.6789	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4580	Approved
0.6784	Remote Similarity	NPD5160	Discontinued
0.6782	Remote Similarity	NPD1914	Approved
0.6774	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1039	Discontinued
0.6763	Remote Similarity	NPD2874	Phase 2
0.6763	Remote Similarity	NPD3645	Discontinued
0.6761	Remote Similarity	NPD4678	Approved
0.6761	Remote Similarity	NPD4675	Approved
0.6757	Remote Similarity	NPD6042	Phase 2
0.6757	Remote Similarity	NPD42	Phase 2
0.6755	Remote Similarity	NPD2968	Approved
0.6755	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2971	Approved
0.6753	Remote Similarity	NPD5582	Discontinued
0.675	Remote Similarity	NPD1669	Approved
0.6744	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2904	Discontinued
0.6734	Remote Similarity	NPD4583	Approved
0.6734	Remote Similarity	NPD4582	Approved
0.6727	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2156	Approved
0.6726	Remote Similarity	NPD2154	Approved
0.6726	Remote Similarity	NPD2155	Approved
0.6724	Remote Similarity	NPD7526	Approved
0.6724	Remote Similarity	NPD52	Approved
0.6724	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7438	Suspended
0.6722	Remote Similarity	NPD4055	Discovery
0.6721	Remote Similarity	NPD4083	Discontinued
0.6709	Remote Similarity	NPD2667	Approved
0.6709	Remote Similarity	NPD2668	Approved
0.6704	Remote Similarity	NPD5977	Approved
0.6704	Remote Similarity	NPD5978	Approved
0.6702	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2232	Approved
0.6687	Remote Similarity	NPD2233	Approved
0.6687	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2230	Approved
0.6687	Remote Similarity	NPD3620	Phase 2
0.6686	Remote Similarity	NPD2677	Approved
0.6685	Remote Similarity	NPD5720	Discontinued
0.6685	Remote Similarity	NPD4227	Discontinued
0.6684	Remote Similarity	NPD4420	Approved
0.6683	Remote Similarity	NPD4004	Approved
0.6683	Remote Similarity	NPD4002	Approved
0.6667	Remote Similarity	NPD7019	Approved
0.6667	Remote Similarity	NPD6747	Phase 1
0.6667	Remote Similarity	NPD597	Approved
0.6667	Remote Similarity	NPD7020	Approved
0.6667	Remote Similarity	NPD601	Approved
0.6667	Remote Similarity	NPD4482	Phase 3
0.6667	Remote Similarity	NPD598	Approved
0.6667	Remote Similarity	NPD3638	Discontinued
0.6649	Remote Similarity	NPD7038	Approved
0.6649	Remote Similarity	NPD7039	Approved
0.6649	Remote Similarity	NPD4951	Discontinued
0.6647	Remote Similarity	NPD6666	Approved
0.6647	Remote Similarity	NPD6667	Approved
0.6647	Remote Similarity	NPD1375	Discontinued
0.6647	Remote Similarity	NPD7124	Phase 2

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