NPASS Compound

Structure

CID195841 OpenBabel06191715582D 25 29 0 0 1 0 0 0 0 0999 V2000 -1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -3.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -4.6180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 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 23 1 0 0 0 0 4 5 1 0 0 0 0 4 14 2 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 1 1 6 0 0 0 13 17 1 0 0 0 0 13 25 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 1 0 0 0 16 5 1 1 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 22 1 6 0 0 0 18 21 1 6 0 0 0 19 22 1 6 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 21 2 1 6 0 0 0 22 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	343.25
Volume:	369.59
LogP:	4.191
LogD:	3.825
LogS:	-4.406
# Rotatable Bonds:	1
TPSA:	38.33
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	5.116
Fsp3:	0.864
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:	-4.671
MDCK Permeability:	2.6268859073752537e-05
Pgp-inhibitor:	0.832
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.148
30% Bioavailability (F30%):	0.144

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.724
Plasma Protein Binding (PPB):	68.3482666015625%
Volume Distribution (VD):	0.877
Pgp-substrate:	21.581249237060547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.403
CYP1A2-substrate:	0.263
CYP2C19-inhibitor:	0.375
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.901
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.42

ADMET: Excretion

Clearance (CL):	9.654
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.902
Human Hepatotoxicity (H-HT):	0.545
Drug-inuced Liver Injury (DILI):	0.791
AMES Toxicity:	0.143
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.952
Carcinogencity:	0.721
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC195841

Natural Product ID:	NPC195841
*Common Name:**	RSFPISDAJMWREU-UACFYWDWSA-N
IUPAC Name:	n.a.
Synonyms:	N-Methylgitingensine
Standard InCHIKey:	RSFPISDAJMWREU-UACFYWDWSA-N
Standard InCHI:	InChI=1S/C22H33NO2/c1-13-17-6-7-19-16-5-4-14-12-15(23-3)8-10-21(14,2)18(16)9-11-22(17,19)20(24)25-13/h4,13,15-19,23H,5-12H2,1-3H3/t13-,15+,16+,17+,18-,19-,21-,22-/m0/s1
SMILES:	CN[C@@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]24[C@H]3CC[C@@H]4[C@@H](OC2=O)C)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801975
PubChem CID:	53262736
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO30860	Kibatalia laurifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443172]
NPO30860	Kibatalia laurifolia	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21443172]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	21000.0	nM	PMID[456488]

☑ 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 NPC195841 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	89
0.1-0.2	741
0.2-0.3	7447
0.3-0.4	16073
0.4-0.5	9217
0.5-0.6	7417
0.6-0.7	1626
0.7-0.8	72
0.8-0.85	6
0.85-0.9	5
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233256
0.9485	High Similarity	NPC239768
0.9485	High Similarity	NPC128698
0.8899	High Similarity	NPC35037
0.8738	High Similarity	NPC119329
0.8598	High Similarity	NPC79238
0.8505	High Similarity	NPC472313
0.8426	Intermediate Similarity	NPC474459
0.8349	Intermediate Similarity	NPC474452
0.8333	Intermediate Similarity	NPC63511
0.8131	Intermediate Similarity	NPC86906
0.8113	Intermediate Similarity	NPC98765
0.7959	Intermediate Similarity	NPC470223
0.7921	Intermediate Similarity	NPC84171
0.79	Intermediate Similarity	NPC28227
0.7857	Intermediate Similarity	NPC100391
0.7755	Intermediate Similarity	NPC21667
0.7686	Intermediate Similarity	NPC478136
0.7624	Intermediate Similarity	NPC167877
0.76	Intermediate Similarity	NPC75810
0.7596	Intermediate Similarity	NPC470224
0.7568	Intermediate Similarity	NPC244982
0.7568	Intermediate Similarity	NPC476756
0.7525	Intermediate Similarity	NPC264127
0.7477	Intermediate Similarity	NPC474164
0.7459	Intermediate Similarity	NPC96010
0.7459	Intermediate Similarity	NPC317654
0.7434	Intermediate Similarity	NPC147835
0.7434	Intermediate Similarity	NPC85001
0.7434	Intermediate Similarity	NPC95920
0.7434	Intermediate Similarity	NPC253645
0.7383	Intermediate Similarity	NPC322063
0.7379	Intermediate Similarity	NPC472220
0.7379	Intermediate Similarity	NPC97884
0.7364	Intermediate Similarity	NPC176012
0.7358	Intermediate Similarity	NPC476754
0.7353	Intermediate Similarity	NPC195640
0.7353	Intermediate Similarity	NPC470050
0.7353	Intermediate Similarity	NPC470051
0.7315	Intermediate Similarity	NPC475894
0.7273	Intermediate Similarity	NPC170038
0.7264	Intermediate Similarity	NPC476752
0.7264	Intermediate Similarity	NPC476753
0.7264	Intermediate Similarity	NPC93027
0.7255	Intermediate Similarity	NPC323765
0.7248	Intermediate Similarity	NPC153792
0.7248	Intermediate Similarity	NPC271387
0.7241	Intermediate Similarity	NPC124358
0.7238	Intermediate Similarity	NPC471896
0.7232	Intermediate Similarity	NPC475239
0.7217	Intermediate Similarity	NPC72753
0.7212	Intermediate Similarity	NPC474845
0.7207	Intermediate Similarity	NPC58200
0.7196	Intermediate Similarity	NPC56525
0.7184	Intermediate Similarity	NPC155011
0.7182	Intermediate Similarity	NPC135799
0.7172	Intermediate Similarity	NPC153987
0.7172	Intermediate Similarity	NPC44083
0.7172	Intermediate Similarity	NPC118987
0.717	Intermediate Similarity	NPC154101
0.717	Intermediate Similarity	NPC218301
0.7168	Intermediate Similarity	NPC230677
0.7155	Intermediate Similarity	NPC66862
0.7143	Intermediate Similarity	NPC474570
0.7143	Intermediate Similarity	NPC478139
0.713	Intermediate Similarity	NPC469599
0.7129	Intermediate Similarity	NPC240302
0.7117	Intermediate Similarity	NPC474348
0.7115	Intermediate Similarity	NPC474684
0.7115	Intermediate Similarity	NPC142361
0.7075	Intermediate Similarity	NPC148414
0.7075	Intermediate Similarity	NPC175628
0.7075	Intermediate Similarity	NPC111585
0.7071	Intermediate Similarity	NPC35574
0.7064	Intermediate Similarity	NPC307164
0.7059	Intermediate Similarity	NPC470047
0.7059	Intermediate Similarity	NPC470538
0.7059	Intermediate Similarity	NPC304646
0.7059	Intermediate Similarity	NPC470046
0.7059	Intermediate Similarity	NPC28280
0.7054	Intermediate Similarity	NPC476755
0.7037	Intermediate Similarity	NPC159410
0.7037	Intermediate Similarity	NPC472223
0.7037	Intermediate Similarity	NPC472224
0.703	Intermediate Similarity	NPC118329
0.703	Intermediate Similarity	NPC152039
0.703	Intermediate Similarity	NPC474955
0.703	Intermediate Similarity	NPC147066
0.703	Intermediate Similarity	NPC329782
0.7009	Intermediate Similarity	NPC150383
0.7009	Intermediate Similarity	NPC26888
0.7	Intermediate Similarity	NPC292133
0.6991	Remote Similarity	NPC36688
0.6991	Remote Similarity	NPC36321
0.6991	Remote Similarity	NPC140723
0.699	Remote Similarity	NPC109512
0.699	Remote Similarity	NPC165064
0.6981	Remote Similarity	NPC475921
0.6981	Remote Similarity	NPC474889
0.6981	Remote Similarity	NPC474704
0.6972	Remote Similarity	NPC174117
0.6964	Remote Similarity	NPC118275
0.6961	Remote Similarity	NPC100297
0.6961	Remote Similarity	NPC472312
0.696	Remote Similarity	NPC237286
0.6952	Remote Similarity	NPC187376
0.6952	Remote Similarity	NPC233836
0.6952	Remote Similarity	NPC96496
0.6952	Remote Similarity	NPC159046
0.6949	Remote Similarity	NPC80834
0.6949	Remote Similarity	NPC469968
0.6944	Remote Similarity	NPC141497
0.6944	Remote Similarity	NPC170220
0.6944	Remote Similarity	NPC107674
0.6944	Remote Similarity	NPC470376
0.6944	Remote Similarity	NPC49776
0.6944	Remote Similarity	NPC474436
0.6944	Remote Similarity	NPC470375
0.6944	Remote Similarity	NPC63118
0.6942	Remote Similarity	NPC470276
0.6937	Remote Similarity	NPC252295
0.6937	Remote Similarity	NPC91604
0.693	Remote Similarity	NPC164835
0.693	Remote Similarity	NPC255309
0.693	Remote Similarity	NPC472228
0.693	Remote Similarity	NPC228669
0.693	Remote Similarity	NPC212874
0.693	Remote Similarity	NPC472227
0.693	Remote Similarity	NPC471293
0.6923	Remote Similarity	NPC311769
0.6923	Remote Similarity	NPC474218
0.6923	Remote Similarity	NPC182106
0.6916	Remote Similarity	NPC44240
0.6909	Remote Similarity	NPC111684
0.6909	Remote Similarity	NPC476903
0.6909	Remote Similarity	NPC58052
0.69	Remote Similarity	NPC4827
0.6897	Remote Similarity	NPC159367
0.6887	Remote Similarity	NPC294480
0.6887	Remote Similarity	NPC226863
0.6881	Remote Similarity	NPC471720
0.6881	Remote Similarity	NPC294266
0.6875	Remote Similarity	NPC476303
0.6875	Remote Similarity	NPC470906
0.687	Remote Similarity	NPC96377
0.6869	Remote Similarity	NPC41017
0.6863	Remote Similarity	NPC232625
0.6863	Remote Similarity	NPC475665
0.6863	Remote Similarity	NPC201912
0.6863	Remote Similarity	NPC38350
0.6857	Remote Similarity	NPC9892
0.6857	Remote Similarity	NPC325594
0.6857	Remote Similarity	NPC10005
0.6857	Remote Similarity	NPC91525
0.6857	Remote Similarity	NPC55309
0.6857	Remote Similarity	NPC28252
0.6857	Remote Similarity	NPC329943
0.6852	Remote Similarity	NPC212301
0.6852	Remote Similarity	NPC190442
0.6852	Remote Similarity	NPC49420
0.6852	Remote Similarity	NPC189520
0.6852	Remote Similarity	NPC110657
0.6852	Remote Similarity	NPC297265
0.6852	Remote Similarity	NPC86266
0.6847	Remote Similarity	NPC140300
0.6847	Remote Similarity	NPC187159
0.6847	Remote Similarity	NPC23680
0.6847	Remote Similarity	NPC107243
0.6847	Remote Similarity	NPC57416
0.6837	Remote Similarity	NPC166797
0.6833	Remote Similarity	NPC135431
0.6832	Remote Similarity	NPC471475
0.6832	Remote Similarity	NPC477371
0.6827	Remote Similarity	NPC85774
0.6827	Remote Similarity	NPC312660
0.6827	Remote Similarity	NPC139566
0.6827	Remote Similarity	NPC59453
0.6827	Remote Similarity	NPC82902
0.6827	Remote Similarity	NPC221758
0.6827	Remote Similarity	NPC475509
0.6827	Remote Similarity	NPC214043
0.6822	Remote Similarity	NPC474679
0.6822	Remote Similarity	NPC77168
0.6822	Remote Similarity	NPC102414
0.6822	Remote Similarity	NPC54689
0.6822	Remote Similarity	NPC84271
0.6822	Remote Similarity	NPC215029
0.6822	Remote Similarity	NPC476733
0.6822	Remote Similarity	NPC305039
0.6818	Remote Similarity	NPC33473
0.6818	Remote Similarity	NPC279974
0.6818	Remote Similarity	NPC184848
0.6818	Remote Similarity	NPC69548
0.6814	Remote Similarity	NPC474327
0.681	Remote Similarity	NPC220974
0.681	Remote Similarity	NPC59530
0.68	Remote Similarity	NPC472300
0.6796	Remote Similarity	NPC321289
0.6796	Remote Similarity	NPC133391
0.6796	Remote Similarity	NPC260956

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 NPC195841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	80
0.1-0.2	470
0.2-0.3	3074
0.3-0.4	3901
0.4-0.5	1057
0.5-0.6	428
0.6-0.7	127
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8058	Intermediate Similarity	NPD5349	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6903	Approved
0.7353	Intermediate Similarity	NPD7521	Approved
0.7353	Intermediate Similarity	NPD6684	Approved
0.7353	Intermediate Similarity	NPD6409	Approved
0.7353	Intermediate Similarity	NPD7146	Approved
0.7353	Intermediate Similarity	NPD5330	Approved
0.7353	Intermediate Similarity	NPD7334	Approved
0.7264	Intermediate Similarity	NPD6399	Phase 3
0.7212	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6672	Approved
0.7212	Intermediate Similarity	NPD5737	Approved
0.713	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6098	Approved
0.6949	Remote Similarity	NPD7335	Phase 2
0.6949	Remote Similarity	NPD7336	Phase 2
0.6949	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5207	Approved
0.6881	Remote Similarity	NPD6001	Approved
0.6827	Remote Similarity	NPD4786	Approved
0.6822	Remote Similarity	NPD6673	Approved
0.6822	Remote Similarity	NPD6080	Approved
0.6822	Remote Similarity	NPD6904	Approved
0.6729	Remote Similarity	NPD5208	Approved
0.6724	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD6083	Phase 2
0.6696	Remote Similarity	NPD6084	Phase 2
0.664	Remote Similarity	NPD6908	Approved
0.664	Remote Similarity	NPD6909	Approved
0.6637	Remote Similarity	NPD5696	Approved
0.6635	Remote Similarity	NPD3667	Approved
0.6613	Remote Similarity	NPD7518	Approved
0.6613	Remote Similarity	NPD7519	Approved
0.6613	Remote Similarity	NPD7517	Approved
0.6577	Remote Similarity	NPD7900	Approved
0.6577	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7147	Phase 3
0.6552	Remote Similarity	NPD6052	Approved
0.6545	Remote Similarity	NPD8035	Phase 2
0.6545	Remote Similarity	NPD5693	Phase 1
0.6545	Remote Similarity	NPD8034	Phase 2
0.6545	Remote Similarity	NPD6050	Approved
0.6542	Remote Similarity	NPD3618	Phase 1
0.6535	Remote Similarity	NPD7122	Discontinued
0.6518	Remote Similarity	NPD5695	Phase 3
0.6514	Remote Similarity	NPD5328	Approved
0.6514	Remote Similarity	NPD6051	Approved
0.6509	Remote Similarity	NPD3666	Approved
0.6509	Remote Similarity	NPD3668	Phase 3
0.6509	Remote Similarity	NPD3133	Approved
0.6509	Remote Similarity	NPD3665	Phase 1
0.6471	Remote Similarity	NPD7320	Approved
0.6462	Remote Similarity	NPD8337	Approved
0.6462	Remote Similarity	NPD8336	Approved
0.6455	Remote Similarity	NPD5692	Phase 3
0.6449	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5739	Approved
0.6441	Remote Similarity	NPD6402	Approved
0.6441	Remote Similarity	NPD7128	Approved
0.6441	Remote Similarity	NPD6675	Approved
0.6441	Remote Similarity	NPD7333	Discontinued
0.6435	Remote Similarity	NPD6404	Discontinued
0.6429	Remote Similarity	NPD7748	Approved
0.6417	Remote Similarity	NPD6373	Approved
0.6417	Remote Similarity	NPD6372	Approved
0.6404	Remote Similarity	NPD7902	Approved
0.6396	Remote Similarity	NPD6079	Approved
0.6396	Remote Similarity	NPD5694	Approved
0.6391	Remote Similarity	NPD8449	Approved
0.6381	Remote Similarity	NPD857	Phase 3
0.6364	Remote Similarity	NPD7751	Phase 1
0.6343	Remote Similarity	NPD8450	Suspended
0.6333	Remote Similarity	NPD6899	Approved
0.6333	Remote Similarity	NPD6881	Approved
0.6321	Remote Similarity	NPD4223	Phase 3
0.6321	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4221	Approved
0.6311	Remote Similarity	NPD6649	Approved
0.6311	Remote Similarity	NPD6650	Approved
0.6296	Remote Similarity	NPD5329	Approved
0.6296	Remote Similarity	NPD1694	Approved
0.6283	Remote Similarity	NPD5707	Approved
0.6283	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD5284	Approved
0.6241	Remote Similarity	NPD6914	Discontinued
0.6239	Remote Similarity	NPD8308	Discontinued
0.6239	Remote Similarity	NPD5279	Phase 3
0.623	Remote Similarity	NPD7102	Approved
0.623	Remote Similarity	NPD7290	Approved
0.623	Remote Similarity	NPD6883	Approved
0.623	Remote Similarity	NPD6420	Discontinued
0.6216	Remote Similarity	NPD4753	Phase 2
0.6207	Remote Similarity	NPD7638	Approved
0.6204	Remote Similarity	NPD4197	Approved
0.62	Remote Similarity	NPD4747	Approved
0.6198	Remote Similarity	NPD6011	Approved
0.6195	Remote Similarity	NPD4202	Approved
0.6182	Remote Similarity	NPD3573	Approved
0.6179	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD8130	Phase 1
0.6179	Remote Similarity	NPD6869	Approved
0.6179	Remote Similarity	NPD6847	Approved
0.6179	Remote Similarity	NPD6617	Approved
0.6174	Remote Similarity	NPD7732	Phase 3
0.6174	Remote Similarity	NPD4697	Phase 3
0.6154	Remote Similarity	NPD8418	Phase 2
0.6154	Remote Similarity	NPD7640	Approved
0.6154	Remote Similarity	NPD7639	Approved
0.6148	Remote Similarity	NPD6012	Approved
0.6148	Remote Similarity	NPD6845	Suspended
0.6148	Remote Similarity	NPD6013	Approved
0.6148	Remote Similarity	NPD6014	Approved
0.6139	Remote Similarity	NPD5777	Approved
0.6129	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD8078	Approved
0.6129	Remote Similarity	NPD8297	Approved
0.6129	Remote Similarity	NPD8077	Approved
0.6117	Remote Similarity	NPD6942	Approved
0.6117	Remote Similarity	NPD7339	Approved
0.6116	Remote Similarity	NPD6614	Approved
0.6111	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4766	Approved
0.6111	Remote Similarity	NPD7755	Approved
0.6111	Remote Similarity	NPD7754	Approved
0.61	Remote Similarity	NPD4137	Phase 3
0.6091	Remote Similarity	NPD4690	Approved
0.6091	Remote Similarity	NPD4689	Approved
0.6091	Remote Similarity	NPD4693	Phase 3
0.6091	Remote Similarity	NPD4138	Approved
0.6091	Remote Similarity	NPD4688	Approved
0.6091	Remote Similarity	NPD5205	Approved
0.6087	Remote Similarity	NPD5210	Approved
0.6087	Remote Similarity	NPD4629	Approved
0.6087	Remote Similarity	NPD5654	Approved
0.6063	Remote Similarity	NPD7115	Discovery
0.6053	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4691	Approved
0.6034	Remote Similarity	NPD5221	Approved
0.6034	Remote Similarity	NPD5222	Approved
0.6034	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6920	Discontinued
0.6031	Remote Similarity	NPD7604	Phase 2
0.6029	Remote Similarity	NPD8338	Approved
0.6019	Remote Similarity	NPD5733	Approved
0.6018	Remote Similarity	NPD4096	Approved
0.6	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6868	Approved
0.5984	Remote Similarity	NPD6412	Phase 2
0.5983	Remote Similarity	NPD4755	Approved
0.5983	Remote Similarity	NPD5959	Approved
0.5983	Remote Similarity	NPD5173	Approved
0.5969	Remote Similarity	NPD6065	Approved
0.5965	Remote Similarity	NPD6411	Approved
0.5963	Remote Similarity	NPD4788	Approved
0.5956	Remote Similarity	NPD7260	Phase 2
0.5952	Remote Similarity	NPD7094	Approved
0.5952	Remote Similarity	NPD6858	Approved
0.5946	Remote Similarity	NPD5280	Approved
0.5946	Remote Similarity	NPD5690	Phase 2
0.5946	Remote Similarity	NPD4694	Approved
0.5946	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD3617	Approved
0.5935	Remote Similarity	NPD6415	Discontinued
0.5929	Remote Similarity	NPD6334	Approved
0.5929	Remote Similarity	NPD6333	Approved
0.5905	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD8040	Discontinued
0.5897	Remote Similarity	NPD7614	Phase 1
0.5891	Remote Similarity	NPD6335	Approved
0.5882	Remote Similarity	NPD4700	Approved
0.5882	Remote Similarity	NPD5285	Approved
0.5882	Remote Similarity	NPD4696	Approved
0.5882	Remote Similarity	NPD5286	Approved
0.5865	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7492	Approved
0.5865	Remote Similarity	NPD4687	Approved
0.5865	Remote Similarity	NPD4058	Approved
0.5862	Remote Similarity	NPD5771	Approved
0.5859	Remote Similarity	NPD6274	Approved
0.5857	Remote Similarity	NPD6623	Phase 3
0.5847	Remote Similarity	NPD7919	Phase 3
0.5847	Remote Similarity	NPD7920	Phase 3
0.5846	Remote Similarity	NPD7100	Approved
0.5846	Remote Similarity	NPD7101	Approved
0.5833	Remote Similarity	NPD7525	Registered
0.5833	Remote Similarity	NPD5223	Approved
0.5827	Remote Similarity	NPD8298	Phase 2
0.5827	Remote Similarity	NPD2607	Approved
0.5827	Remote Similarity	NPD4632	Approved
0.5826	Remote Similarity	NPD7637	Suspended
0.5825	Remote Similarity	NPD5276	Approved
0.5825	Remote Similarity	NPD4243	Approved
0.5822	Remote Similarity	NPD7487	Discontinued
0.5821	Remote Similarity	NPD6616	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