NPASS Compound

Structure

CID243626 OpenBabel06191716042D 26 30 0 0 1 0 0 0 0 0999 V2000 -5.0481 2.0670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2106 1.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5222 -0.8265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1346 2.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7472 2.8904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1955 2.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 1.2577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7043 2.1950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7043 0.5769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4835 1.1229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5076 2.2409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3745 2.1950 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7867 1.3859 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3777 1.5733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3255 1.8859 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3745 0.5769 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3827 0.9239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2304 1.7210 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9969 0.0785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2304 1.0508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3255 0.8859 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6464 -0.6819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4502 2.5747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5225 -0.8526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1396 1.3300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 10 26 1 0 0 0 0 11 24 1 0 0 0 0 12 8 1 6 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 10 1 6 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 4 1 6 0 0 0 15 21 1 0 0 0 0 16 9 1 6 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 6 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 9 1 1 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.19
Volume:	358.302
LogP:	3.232
LogD:	2.858
LogS:	-5.032
# Rotatable Bonds:	3
TPSA:	60.03
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.896
Synthetic Accessibility Score:	6.323
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.243
MDCK Permeability:	1.0905829185503535e-05
Pgp-inhibitor:	0.898
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.657

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.78
Plasma Protein Binding (PPB):	15.81362533569336%
Volume Distribution (VD):	1.54
Pgp-substrate:	66.08477783203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.792
CYP2C19-inhibitor:	0.319
CYP2C19-substrate:	0.934
CYP2C9-inhibitor:	0.146
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.61
CYP3A4-inhibitor:	0.7
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	9.205
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.941
Human Hepatotoxicity (H-HT):	0.401
Drug-inuced Liver Injury (DILI):	0.715
AMES Toxicity:	0.826
Rat Oral Acute Toxicity:	0.787
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.552
Carcinogencity:	0.79
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC243626

Natural Product ID:	NPC243626
*Common Name:**	Gelsemicine
IUPAC Name:	n.a.
Synonyms:	Gelsemicine
Standard InCHIKey:	RIHQHYIWKHVLRH-XKTBTPLDSA-N
Standard InCHI:	InChI=1S/C20H26N2O4/c1-4-15-12-8-18-20(9-16(21-15)13(12)10-26-18)14-6-5-11(24-2)7-17(14)22(25-3)19(20)23/h5-7,12-13,15-16,18,21H,4,8-10H2,1-3H3/p+1/t12-,13+,15-,16+,18-,20+/m1/s1
SMILES:	CC[C@@H]1[C@@H]2C[C@@H]3[C@]4(C[C@@H]([C@H]2CO3)[NH2+]1)c1ccc(cc1N(C4=O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523430
PubChem CID:	5462428
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003758] Gelsemium alkaloids

*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
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643063]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989532]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24256496]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	leaves and vine stems	Xishuangbanna Tropical Botanical Garden (XTBG), Chinese Academy of Science (CAS), Mengla County, Yunnan Province, China	2009-OCT	PMID[26103517]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222693]
NPO12651	Gelsemium sempervirens	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3655795]
NPO12651	Gelsemium sempervirens	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12651	Gelsemium sempervirens	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12651	Gelsemium sempervirens	Species	Gelsemiaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT762	Cell Line	A-431	Homo sapiens	EC50	=	750.0	nM	PMID[486376]

☑ 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 NPC243626 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	332
0.1-0.2	1663
0.2-0.3	7685
0.3-0.4	10009
0.4-0.5	16759
0.5-0.6	5234
0.6-0.7	931
0.7-0.8	71
0.8-0.85	3
0.85-0.9	4
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9657	High Similarity	NPC230313
0.9209	High Similarity	NPC473008
0.9135	High Similarity	NPC477161
0.9106	High Similarity	NPC473004
0.8989	High Similarity	NPC477160
0.8983	High Similarity	NPC473007
0.8757	High Similarity	NPC100863
0.8677	High Similarity	NPC14339
0.8608	High Similarity	NPC473006
0.8605	High Similarity	NPC286871
0.8377	Intermediate Similarity	NPC473005
0.8368	Intermediate Similarity	NPC67904
0.8182	Intermediate Similarity	NPC176983
0.8069	Intermediate Similarity	NPC77777
0.8042	Intermediate Similarity	NPC22476
0.8	Intermediate Similarity	NPC159815
0.799	Intermediate Similarity	NPC138830
0.7989	Intermediate Similarity	NPC473569
0.7989	Intermediate Similarity	NPC474059
0.7955	Intermediate Similarity	NPC29285
0.791	Intermediate Similarity	NPC10732
0.7828	Intermediate Similarity	NPC87714
0.7812	Intermediate Similarity	NPC204970
0.7766	Intermediate Similarity	NPC477159
0.7739	Intermediate Similarity	NPC475147
0.7729	Intermediate Similarity	NPC10653
0.7729	Intermediate Similarity	NPC318525
0.7722	Intermediate Similarity	NPC143457
0.7673	Intermediate Similarity	NPC475133
0.7667	Intermediate Similarity	NPC122886
0.7626	Intermediate Similarity	NPC127178
0.7577	Intermediate Similarity	NPC203628
0.7573	Intermediate Similarity	NPC189661
0.7565	Intermediate Similarity	NPC284706
0.7561	Intermediate Similarity	NPC127996
0.754	Intermediate Similarity	NPC13367
0.75	Intermediate Similarity	NPC126556
0.75	Intermediate Similarity	NPC195636
0.75	Intermediate Similarity	NPC232600
0.7476	Intermediate Similarity	NPC119722
0.7463	Intermediate Similarity	NPC269449
0.7459	Intermediate Similarity	NPC214960
0.7459	Intermediate Similarity	NPC279527
0.7436	Intermediate Similarity	NPC174629
0.7432	Intermediate Similarity	NPC309531
0.7432	Intermediate Similarity	NPC472102
0.7427	Intermediate Similarity	NPC82541
0.7426	Intermediate Similarity	NPC41216
0.7424	Intermediate Similarity	NPC303214
0.7418	Intermediate Similarity	NPC231924
0.7393	Intermediate Similarity	NPC476069
0.7358	Intermediate Similarity	NPC128476
0.7352	Intermediate Similarity	NPC291173
0.7333	Intermediate Similarity	NPC21425
0.7333	Intermediate Similarity	NPC305984
0.7317	Intermediate Similarity	NPC478075
0.7299	Intermediate Similarity	NPC473041
0.7268	Intermediate Similarity	NPC195787
0.7268	Intermediate Similarity	NPC246140
0.7268	Intermediate Similarity	NPC245741
0.7264	Intermediate Similarity	NPC219397
0.7264	Intermediate Similarity	NPC288110
0.7256	Intermediate Similarity	NPC19175
0.724	Intermediate Similarity	NPC184680
0.7217	Intermediate Similarity	NPC303658
0.7211	Intermediate Similarity	NPC251212
0.7211	Intermediate Similarity	NPC214626
0.7211	Intermediate Similarity	NPC73280
0.7211	Intermediate Similarity	NPC139085
0.7207	Intermediate Similarity	NPC470785
0.7207	Intermediate Similarity	NPC470784
0.7204	Intermediate Similarity	NPC234772
0.7196	Intermediate Similarity	NPC46259
0.7194	Intermediate Similarity	NPC282092
0.7188	Intermediate Similarity	NPC260075
0.7176	Intermediate Similarity	NPC115588
0.7172	Intermediate Similarity	NPC105055
0.7172	Intermediate Similarity	NPC5630
0.7172	Intermediate Similarity	NPC22689
0.7143	Intermediate Similarity	NPC470481
0.7143	Intermediate Similarity	NPC470482
0.7135	Intermediate Similarity	NPC469428
0.7135	Intermediate Similarity	NPC113946
0.7129	Intermediate Similarity	NPC161804
0.7128	Intermediate Similarity	NPC70172
0.7128	Intermediate Similarity	NPC314659
0.712	Intermediate Similarity	NPC96901
0.7117	Intermediate Similarity	NPC154922
0.7113	Intermediate Similarity	NPC70092
0.7113	Intermediate Similarity	NPC39822
0.711	Intermediate Similarity	NPC470480
0.7104	Intermediate Similarity	NPC473105
0.7087	Intermediate Similarity	NPC207971
0.7085	Intermediate Similarity	NPC283207
0.7078	Intermediate Similarity	NPC194740
0.7077	Intermediate Similarity	NPC197335
0.7065	Intermediate Similarity	NPC470485
0.7056	Intermediate Similarity	NPC102760
0.7053	Intermediate Similarity	NPC268077
0.7037	Intermediate Similarity	NPC299582
0.7037	Intermediate Similarity	NPC472106
0.7032	Intermediate Similarity	NPC473458
0.7023	Intermediate Similarity	NPC222046
0.7021	Intermediate Similarity	NPC472101
0.7021	Intermediate Similarity	NPC472117
0.7021	Intermediate Similarity	NPC472120
0.701	Intermediate Similarity	NPC71124
0.701	Intermediate Similarity	NPC186669
0.7	Intermediate Similarity	NPC45389
0.7	Intermediate Similarity	NPC311906
0.699	Remote Similarity	NPC28368
0.6986	Remote Similarity	NPC198160
0.6986	Remote Similarity	NPC476436
0.6982	Remote Similarity	NPC139373
0.6978	Remote Similarity	NPC151171
0.6977	Remote Similarity	NPC96321
0.6974	Remote Similarity	NPC81939
0.6971	Remote Similarity	NPC470484
0.6968	Remote Similarity	NPC223242
0.6965	Remote Similarity	NPC1820
0.6965	Remote Similarity	NPC470483
0.6963	Remote Similarity	NPC470001
0.6963	Remote Similarity	NPC470002
0.6963	Remote Similarity	NPC148183
0.6963	Remote Similarity	NPC152768
0.6961	Remote Similarity	NPC302548
0.696	Remote Similarity	NPC469722
0.696	Remote Similarity	NPC113455
0.6959	Remote Similarity	NPC264482
0.6959	Remote Similarity	NPC203202
0.6957	Remote Similarity	NPC1464
0.6949	Remote Similarity	NPC106606
0.6944	Remote Similarity	NPC37957
0.6943	Remote Similarity	NPC285622
0.6943	Remote Similarity	NPC475666
0.6942	Remote Similarity	NPC329747
0.6941	Remote Similarity	NPC21638
0.6933	Remote Similarity	NPC131977
0.6931	Remote Similarity	NPC315498
0.6931	Remote Similarity	NPC230942
0.6927	Remote Similarity	NPC251071
0.6915	Remote Similarity	NPC193410
0.6903	Remote Similarity	NPC474183
0.6901	Remote Similarity	NPC264176
0.6901	Remote Similarity	NPC116178
0.6893	Remote Similarity	NPC241263
0.6888	Remote Similarity	NPC6974
0.6888	Remote Similarity	NPC321211
0.6887	Remote Similarity	NPC471304
0.6887	Remote Similarity	NPC476651
0.6886	Remote Similarity	NPC469451
0.6881	Remote Similarity	NPC28510
0.6878	Remote Similarity	NPC248117
0.6878	Remote Similarity	NPC475559
0.6878	Remote Similarity	NPC471513
0.6872	Remote Similarity	NPC475816
0.6872	Remote Similarity	NPC475910
0.6872	Remote Similarity	NPC469450
0.687	Remote Similarity	NPC120239
0.6869	Remote Similarity	NPC471080
0.6869	Remote Similarity	NPC159963
0.6869	Remote Similarity	NPC321166
0.6869	Remote Similarity	NPC217903
0.6869	Remote Similarity	NPC469592
0.6866	Remote Similarity	NPC153923
0.6862	Remote Similarity	NPC61013
0.685	Remote Similarity	NPC87391
0.6845	Remote Similarity	NPC265642
0.6845	Remote Similarity	NPC132874
0.6845	Remote Similarity	NPC138615
0.6845	Remote Similarity	NPC161827
0.6845	Remote Similarity	NPC218733
0.6844	Remote Similarity	NPC160113
0.6844	Remote Similarity	NPC476220
0.6842	Remote Similarity	NPC472121
0.6842	Remote Similarity	NPC473460
0.6831	Remote Similarity	NPC146370
0.683	Remote Similarity	NPC474192
0.683	Remote Similarity	NPC475720
0.683	Remote Similarity	NPC476429
0.6828	Remote Similarity	NPC301501
0.6826	Remote Similarity	NPC329932
0.6825	Remote Similarity	NPC301163
0.6824	Remote Similarity	NPC133609
0.6823	Remote Similarity	NPC471652
0.6822	Remote Similarity	NPC472098
0.682	Remote Similarity	NPC469594
0.6816	Remote Similarity	NPC14994
0.6814	Remote Similarity	NPC254957
0.6814	Remote Similarity	NPC203972
0.6812	Remote Similarity	NPC469452
0.6812	Remote Similarity	NPC5374
0.6806	Remote Similarity	NPC330009
0.6804	Remote Similarity	NPC85482
0.6802	Remote Similarity	NPC218594
0.6802	Remote Similarity	NPC99043
0.68	Remote Similarity	NPC259626
0.68	Remote Similarity	NPC322621
0.68	Remote Similarity	NPC52262
0.6798	Remote Similarity	NPC25401

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 NPC243626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	606
0.2-0.3	830
0.3-0.4	1599
0.4-0.5	3013
0.5-0.6	2531
0.6-0.7	356
0.7-0.8	10
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
0.7989	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6238	Discontinued
0.7663	Intermediate Similarity	NPD5183	Approved
0.7663	Intermediate Similarity	NPD5186	Approved
0.7514	Intermediate Similarity	NPD6457	Approved
0.7351	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5334	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7479	Phase 2
0.715	Intermediate Similarity	NPD3437	Discontinued
0.7143	Intermediate Similarity	NPD3511	Discontinued
0.7123	Intermediate Similarity	NPD4981	Phase 2
0.7101	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD5600	Discontinued
0.7077	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3912	Discontinued
0.7035	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6644	Discontinued
0.6963	Remote Similarity	NPD3983	Phase 3
0.6963	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4796	Discontinued
0.6931	Remote Similarity	NPD1743	Approved
0.6931	Remote Similarity	NPD19	Approved
0.6931	Remote Similarity	NPD1742	Approved
0.6927	Remote Similarity	NPD5071	Phase 2
0.6882	Remote Similarity	NPD6357	Discontinued
0.6875	Remote Similarity	NPD6723	Discontinued
0.6875	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD3479	Discontinued
0.6847	Remote Similarity	NPD5937	Approved
0.6845	Remote Similarity	NPD4668	Phase 2
0.6842	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4166	Phase 2
0.6837	Remote Similarity	NPD5293	Phase 2
0.6837	Remote Similarity	NPD5313	Approved
0.6837	Remote Similarity	NPD7559	Phase 2
0.6837	Remote Similarity	NPD5312	Approved
0.6814	Remote Similarity	NPD4539	Phase 1
0.681	Remote Similarity	NPD4467	Phase 2
0.681	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4465	Phase 2
0.6806	Remote Similarity	NPD1309	Phase 2
0.6806	Remote Similarity	NPD1307	Phase 2
0.6802	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7626	Approved
0.6794	Remote Similarity	NPD7627	Approved
0.6792	Remote Similarity	NPD4859	Phase 1
0.6792	Remote Similarity	NPD4154	Approved
0.6792	Remote Similarity	NPD8027	Approved
0.6784	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1769	Discontinued
0.6769	Remote Similarity	NPD2248	Approved
0.6769	Remote Similarity	NPD2246	Approved
0.6766	Remote Similarity	NPD3153	Approved
0.6766	Remote Similarity	NPD3154	Approved
0.6751	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7280	Phase 3
0.675	Remote Similarity	NPD7281	Phase 3
0.6743	Remote Similarity	NPD5632	Approved
0.6737	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1294	Discontinued
0.6722	Remote Similarity	NPD822	Approved
0.6716	Remote Similarity	NPD5994	Discontinued
0.6712	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4597	Approved
0.6703	Remote Similarity	NPD4598	Approved
0.6701	Remote Similarity	NPD6107	Approved
0.67	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6519	Phase 2
0.6699	Remote Similarity	NPD7256	Discontinued
0.6698	Remote Similarity	NPD3003	Approved
0.6682	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4885	Approved
0.6667	Remote Similarity	NPD5114	Approved
0.6667	Remote Similarity	NPD3793	Phase 3
0.6667	Remote Similarity	NPD3964	Approved
0.6667	Remote Similarity	NPD6321	Discontinued
0.6667	Remote Similarity	NPD5112	Approved
0.6667	Remote Similarity	NPD7820	Phase 3
0.6667	Remote Similarity	NPD5113	Approved
0.6652	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8016	Phase 3
0.6635	Remote Similarity	NPD5515	Phase 2
0.6634	Remote Similarity	NPD6851	Approved
0.6634	Remote Similarity	NPD6853	Approved
0.6633	Remote Similarity	NPD2216	Approved
0.6633	Remote Similarity	NPD2215	Approved
0.6615	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD3592	Approved
0.6605	Remote Similarity	NPD3591	Approved
0.66	Remote Similarity	NPD6878	Phase 2
0.66	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6879	Phase 2
0.66	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6297	Approved
0.6596	Remote Similarity	NPD6030	Approved
0.6596	Remote Similarity	NPD1670	Discontinued
0.6596	Remote Similarity	NPD6031	Approved
0.6595	Remote Similarity	NPD6517	Phase 3
0.6593	Remote Similarity	NPD4952	Phase 3
0.6587	Remote Similarity	NPD5582	Discontinued
0.6585	Remote Similarity	NPD4258	Approved
0.6585	Remote Similarity	NPD4259	Approved
0.6583	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5617	Suspended
0.6578	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7805	Phase 3
0.6575	Remote Similarity	NPD5025	Approved
0.6571	Remote Similarity	NPD1768	Approved
0.6571	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6874	Approved
0.657	Remote Similarity	NPD3631	Phase 3
0.6567	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD4846	Phase 2
0.6564	Remote Similarity	NPD5823	Approved
0.6559	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5658	Approved
0.6557	Remote Similarity	NPD7752	Approved
0.6557	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7753	Approved
0.6557	Remote Similarity	NPD7316	Discontinued
0.6553	Remote Similarity	NPD5641	Discontinued
0.6553	Remote Similarity	NPD8358	Approved
0.6553	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6790	Phase 1
0.6548	Remote Similarity	NPD4083	Discontinued
0.6547	Remote Similarity	NPD8311	Discontinued
0.6545	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD4493	Discontinued
0.6537	Remote Similarity	NPD3349	Phase 2
0.6533	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2247	Approved
0.6531	Remote Similarity	NPD2249	Approved
0.653	Remote Similarity	NPD4679	Discontinued
0.6528	Remote Similarity	NPD3557	Approved
0.6528	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3556	Approved
0.6528	Remote Similarity	NPD5967	Approved
0.6528	Remote Similarity	NPD3558	Approved
0.6528	Remote Similarity	NPD3560	Approved
0.652	Remote Similarity	NPD5256	Discontinued
0.6517	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5997	Discontinued
0.651	Remote Similarity	NPD7248	Discontinued
0.6509	Remote Similarity	NPD7476	Discontinued
0.6508	Remote Similarity	NPD8459	Approved
0.6508	Remote Similarity	NPD3640	Phase 3
0.6508	Remote Similarity	NPD8460	Approved
0.6508	Remote Similarity	NPD3641	Approved
0.6508	Remote Similarity	NPD3639	Approved
0.6507	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4373	Phase 2
0.6505	Remote Similarity	NPD2843	Phase 2
0.6505	Remote Similarity	NPD5928	Phase 1
0.6505	Remote Similarity	NPD2845	Phase 2
0.65	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8149	Discontinued
0.6495	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD2874	Phase 2
0.6489	Remote Similarity	NPD7528	Approved
0.6488	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5637	Discontinued
0.6484	Remote Similarity	NPD743	Approved
0.6482	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD2916	Discontinued
0.6481	Remote Similarity	NPD4082	Approved
0.648	Remote Similarity	NPD8467	Approved
0.648	Remote Similarity	NPD8465	Approved
0.648	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.648	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8466	Approved
0.6477	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5014	Discontinued
0.6471	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6719	Approved
0.6471	Remote Similarity	NPD3141	Discontinued
0.6465	Remote Similarity	NPD5601	Phase 2
0.6465	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6677	Suspended
0.6456	Remote Similarity	NPD3398	Discontinued
0.6455	Remote Similarity	NPD5903	Approved
0.6455	Remote Similarity	NPD5902	Approved
0.645	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2681	Approved
0.6447	Remote Similarity	NPD7126	Discontinued
0.6447	Remote Similarity	NPD2680	Approved
0.6446	Remote Similarity	NPD7955	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