NPASS Compound

Structure

NPC13367 OpenBabel07101719522D 28 32 0 0 1 0 0 0 0 0999 V2000 -0.6932 0.8659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2019 0.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3485 1.6395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6447 0.6895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2012 -2.8821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0393 -2.3982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 -2.3982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0393 -1.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4742 -1.4206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1484 -0.6423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4827 1.1154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9210 -1.4650 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6369 -1.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9678 -0.2227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0088 -1.7880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2012 -0.9466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8957 -0.4976 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3611 -0.1302 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7234 -0.2484 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9624 0.1012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3561 -0.7829 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4196 -1.0203 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 -3.6839 2.0620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9302 1.7773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6475 0.7192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5496 -0.0340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5624 0.8164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 11 1 0 0 0 0 3 26 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 2 0 0 0 0 8 16 2 0 0 0 0 10 27 1 0 0 0 0 11 24 2 0 0 0 0 11 28 1 0 0 0 0 12 10 1 1 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 15 9 1 1 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 14 1 6 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 1 0 0 0 19 21 1 1 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 20 25 2 0 0 0 0 21 9 1 6 0 0 0 23 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.17
Volume:	379.116
LogP:	2.708
LogD:	2.429
LogS:	-4.708
# Rotatable Bonds:	4
TPSA:	77.43
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.746
Synthetic Accessibility Score:	6.314
Fsp3:	0.571
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:	-5.004
MDCK Permeability:	4.1233128285966814e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.721
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.906
Plasma Protein Binding (PPB):	53.10348892211914%
Volume Distribution (VD):	0.99
Pgp-substrate:	33.46706008911133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.594
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.378
CYP3A4-substrate:	0.884

ADMET: Excretion

Clearance (CL):	7.274
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.845
AMES Toxicity:	0.892
Rat Oral Acute Toxicity:	0.614
Maximum Recommended Daily Dose:	0.834
Skin Sensitization:	0.159
Carcinogencity:	0.832
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC13367

Natural Product ID:	NPC13367
*Common Name:**	MLBPCDDHLQCMGP-RAXDMVSQSA-N
IUPAC Name:	n.a.
Synonyms:	14-Acetoxygelsenicine
Standard InCHIKey:	MLBPCDDHLQCMGP-RAXDMVSQSA-N
Standard InCHI:	InChI=1S/C21H24N2O5/c1-4-14-17-12-10-27-19(18(17)28-11(2)24)21(9-15(12)22-14)13-7-5-6-8-16(13)23(26-3)20(21)25/h5-8,12,15,17-19H,4,9-10H2,1-3H3/t12-,15+,17-,18-,19-,21+/m1/s1
SMILES:	CCC1=N[C@H]2C[C@]3(c4ccccc4N(C3=O)OC)[C@H]3[C@@H]([C@@H]1[C@@H]2CO3)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497706
PubChem CID:	11962104
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives

*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]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]

☑ 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	=	250.0	nM	PMID[524820]

☑ 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 NPC13367 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	254
0.1-0.2	1189
0.2-0.3	5118
0.3-0.4	20740
0.4-0.5	11128
0.5-0.6	3759
0.6-0.7	465
0.7-0.8	31
0.8-0.85	5
0.85-0.9	4
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9455	High Similarity	NPC282092
0.9423	High Similarity	NPC143457
0.9217	High Similarity	NPC245741
0.8966	High Similarity	NPC475559
0.8966	High Similarity	NPC302548
0.8634	High Similarity	NPC29285
0.8537	High Similarity	NPC286871
0.8315	Intermediate Similarity	NPC14339
0.8313	Intermediate Similarity	NPC176983
0.8276	Intermediate Similarity	NPC477159
0.8045	Intermediate Similarity	NPC284706
0.7798	Intermediate Similarity	NPC161827
0.7706	Intermediate Similarity	NPC153694
0.7706	Intermediate Similarity	NPC211525
0.7661	Intermediate Similarity	NPC263709
0.7661	Intermediate Similarity	NPC310403
0.7661	Intermediate Similarity	NPC97380
0.7661	Intermediate Similarity	NPC148468
0.7661	Intermediate Similarity	NPC63210
0.7661	Intermediate Similarity	NPC243673
0.7586	Intermediate Similarity	NPC470069
0.7586	Intermediate Similarity	NPC52059
0.7582	Intermediate Similarity	NPC472209
0.7571	Intermediate Similarity	NPC476425
0.754	Intermediate Similarity	NPC243626
0.75	Intermediate Similarity	NPC113946
0.7472	Intermediate Similarity	NPC298851
0.7472	Intermediate Similarity	NPC21752
0.7472	Intermediate Similarity	NPC181138
0.7472	Intermediate Similarity	NPC210415
0.7472	Intermediate Similarity	NPC276993
0.7472	Intermediate Similarity	NPC293255
0.7447	Intermediate Similarity	NPC230313
0.7444	Intermediate Similarity	NPC476326
0.7443	Intermediate Similarity	NPC278887
0.7433	Intermediate Similarity	NPC473004
0.7386	Intermediate Similarity	NPC472106
0.7384	Intermediate Similarity	NPC473297
0.7371	Intermediate Similarity	NPC472101
0.7371	Intermediate Similarity	NPC472120
0.7356	Intermediate Similarity	NPC469461
0.7344	Intermediate Similarity	NPC475489
0.7322	Intermediate Similarity	NPC475962
0.7314	Intermediate Similarity	NPC309531
0.7314	Intermediate Similarity	NPC472102
0.7293	Intermediate Similarity	NPC129624
0.7293	Intermediate Similarity	NPC476441
0.7278	Intermediate Similarity	NPC96901
0.7273	Intermediate Similarity	NPC472121
0.7273	Intermediate Similarity	NPC472117
0.7245	Intermediate Similarity	NPC277350
0.7234	Intermediate Similarity	NPC473008
0.7228	Intermediate Similarity	NPC476428
0.7216	Intermediate Similarity	NPC225319
0.7216	Intermediate Similarity	NPC201424
0.7213	Intermediate Similarity	NPC321211
0.7207	Intermediate Similarity	NPC469462
0.7204	Intermediate Similarity	NPC469460
0.7182	Intermediate Similarity	NPC251212
0.7182	Intermediate Similarity	NPC214626
0.7182	Intermediate Similarity	NPC139085
0.7176	Intermediate Similarity	NPC472100
0.7165	Intermediate Similarity	NPC214428
0.716	Intermediate Similarity	NPC472103
0.7158	Intermediate Similarity	NPC260075
0.7151	Intermediate Similarity	NPC279527
0.7151	Intermediate Similarity	NPC214960
0.7151	Intermediate Similarity	NPC472119
0.7143	Intermediate Similarity	NPC473298
0.7136	Intermediate Similarity	NPC469743
0.7136	Intermediate Similarity	NPC477160
0.7126	Intermediate Similarity	NPC478076
0.7112	Intermediate Similarity	NPC322621
0.7107	Intermediate Similarity	NPC185742
0.7107	Intermediate Similarity	NPC475847
0.7092	Intermediate Similarity	NPC162730
0.7092	Intermediate Similarity	NPC474116
0.7088	Intermediate Similarity	NPC285622
0.7083	Intermediate Similarity	NPC474121
0.7071	Intermediate Similarity	NPC477161
0.7068	Intermediate Similarity	NPC55493
0.703	Intermediate Similarity	NPC475778
0.7022	Intermediate Similarity	NPC474058
0.7022	Intermediate Similarity	NPC315368
0.7021	Intermediate Similarity	NPC473007
0.6995	Remote Similarity	NPC34717
0.6989	Remote Similarity	NPC11149
0.6963	Remote Similarity	NPC314333
0.6963	Remote Similarity	NPC22689
0.6963	Remote Similarity	NPC329858
0.6963	Remote Similarity	NPC105055
0.6947	Remote Similarity	NPC181928
0.6927	Remote Similarity	NPC472097
0.6923	Remote Similarity	NPC90967
0.6912	Remote Similarity	NPC473006
0.6907	Remote Similarity	NPC221687
0.6902	Remote Similarity	NPC177261
0.6894	Remote Similarity	NPC317758
0.6889	Remote Similarity	NPC99632
0.6889	Remote Similarity	NPC476231
0.6889	Remote Similarity	NPC282339
0.6882	Remote Similarity	NPC186669
0.6872	Remote Similarity	NPC97100
0.6872	Remote Similarity	NPC473375
0.6851	Remote Similarity	NPC313757
0.6847	Remote Similarity	NPC234999
0.6842	Remote Similarity	NPC52262
0.6842	Remote Similarity	NPC79062
0.6842	Remote Similarity	NPC472107
0.6839	Remote Similarity	NPC25401
0.6828	Remote Similarity	NPC203202
0.6828	Remote Similarity	NPC264482
0.6824	Remote Similarity	NPC243162
0.6824	Remote Similarity	NPC315051
0.6821	Remote Similarity	NPC116519
0.6809	Remote Similarity	NPC39822
0.6805	Remote Similarity	NPC287358
0.6784	Remote Similarity	NPC471512
0.6778	Remote Similarity	NPC193410
0.6776	Remote Similarity	NPC472114
0.6776	Remote Similarity	NPC472115
0.6771	Remote Similarity	NPC14994
0.6771	Remote Similarity	NPC473815
0.6771	Remote Similarity	NPC472323
0.6769	Remote Similarity	NPC203972
0.6768	Remote Similarity	NPC241024
0.6757	Remote Similarity	NPC355
0.6755	Remote Similarity	NPC6974
0.674	Remote Similarity	NPC248117
0.6737	Remote Similarity	NPC159963
0.6734	Remote Similarity	NPC138830
0.6731	Remote Similarity	NPC244425
0.6731	Remote Similarity	NPC15384
0.6722	Remote Similarity	NPC61013
0.6667	Remote Similarity	NPC259626
0.6667	Remote Similarity	NPC474077
0.6667	Remote Similarity	NPC477157
0.6667	Remote Similarity	NPC473005
0.6667	Remote Similarity	NPC162104
0.6667	Remote Similarity	NPC477156
0.6667	Remote Similarity	NPC99043
0.6667	Remote Similarity	NPC218594
0.665	Remote Similarity	NPC67904
0.6649	Remote Similarity	NPC223595
0.6649	Remote Similarity	NPC167724
0.6649	Remote Similarity	NPC224970
0.6648	Remote Similarity	NPC68650
0.6633	Remote Similarity	NPC204970
0.6633	Remote Similarity	NPC52557
0.6632	Remote Similarity	NPC291759
0.663	Remote Similarity	NPC123241
0.663	Remote Similarity	NPC471124
0.6618	Remote Similarity	NPC10732
0.6615	Remote Similarity	NPC97584
0.6615	Remote Similarity	NPC2933
0.6614	Remote Similarity	NPC234987
0.6613	Remote Similarity	NPC469915
0.6612	Remote Similarity	NPC293458
0.6604	Remote Similarity	NPC2395
0.6596	Remote Similarity	NPC469726
0.6596	Remote Similarity	NPC329338
0.6593	Remote Similarity	NPC36495
0.6589	Remote Similarity	NPC235885
0.6587	Remote Similarity	NPC187231
0.6583	Remote Similarity	NPC162440
0.6583	Remote Similarity	NPC469736
0.6582	Remote Similarity	NPC117244
0.6582	Remote Similarity	NPC473763
0.658	Remote Similarity	NPC133591
0.6579	Remote Similarity	NPC475094
0.6566	Remote Similarity	NPC289299
0.6566	Remote Similarity	NPC57994
0.6564	Remote Similarity	NPC175474
0.6562	Remote Similarity	NPC256288
0.6562	Remote Similarity	NPC472104
0.6561	Remote Similarity	NPC84347
0.6557	Remote Similarity	NPC477158
0.6555	Remote Similarity	NPC474412
0.6552	Remote Similarity	NPC477155
0.655	Remote Similarity	NPC100863
0.655	Remote Similarity	NPC149708
0.6546	Remote Similarity	NPC66210
0.6546	Remote Similarity	NPC207033
0.6546	Remote Similarity	NPC38823
0.6545	Remote Similarity	NPC15840
0.6538	Remote Similarity	NPC159815
0.6538	Remote Similarity	NPC472098
0.6538	Remote Similarity	NPC151976
0.6536	Remote Similarity	NPC243756
0.6528	Remote Similarity	NPC258480
0.6524	Remote Similarity	NPC472118
0.6524	Remote Similarity	NPC204491
0.6517	Remote Similarity	NPC242000
0.6515	Remote Similarity	NPC192306
0.6513	Remote Similarity	NPC21425
0.6507	Remote Similarity	NPC472291
0.6503	Remote Similarity	NPC471122
0.6497	Remote Similarity	NPC28510
0.6493	Remote Similarity	NPC471197
0.6485	Remote Similarity	NPC195461

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 NPC13367 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	508
0.2-0.3	786
0.3-0.4	1738
0.4-0.5	3814
0.5-0.6	2032
0.6-0.7	114
0.7-0.8	1
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
0.7457	Intermediate Similarity	NPD7599	Phase 2
0.7216	Intermediate Similarity	NPD7600	Phase 2
0.7045	Intermediate Similarity	NPD7105	Phase 1
0.7006	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4682	Phase 2
0.6963	Remote Similarity	NPD4499	Approved
0.6854	Remote Similarity	NPD1663	Discontinued
0.6826	Remote Similarity	NPD5182	Approved
0.6826	Remote Similarity	NPD5185	Approved
0.6826	Remote Similarity	NPD5184	Approved
0.6735	Remote Similarity	NPD4427	Phase 2
0.6733	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5942	Approved
0.6705	Remote Similarity	NPD5941	Approved
0.6705	Remote Similarity	NPD2820	Phase 3
0.6684	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2844	Phase 3
0.6648	Remote Similarity	NPD4120	Approved
0.6648	Remote Similarity	NPD4121	Phase 3
0.6647	Remote Similarity	NPD2365	Approved
0.6647	Remote Similarity	NPD4738	Phase 2
0.6634	Remote Similarity	NPD6176	Phase 1
0.6611	Remote Similarity	NPD5742	Approved
0.6611	Remote Similarity	NPD5743	Approved
0.6611	Remote Similarity	NPD5741	Approved
0.661	Remote Similarity	NPD4432	Discontinued
0.66	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5003	Discontinued
0.6569	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7001	Phase 3
0.6566	Remote Similarity	NPD4602	Approved
0.6559	Remote Similarity	NPD6457	Approved
0.6553	Remote Similarity	NPD4506	Discontinued
0.655	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6878	Phase 2
0.6545	Remote Similarity	NPD6879	Phase 2
0.6519	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5076	Approved
0.6497	Remote Similarity	NPD5077	Approved
0.6485	Remote Similarity	NPD4600	Approved
0.6485	Remote Similarity	NPD4601	Approved
0.648	Remote Similarity	NPD4334	Discontinued
0.6468	Remote Similarity	NPD7777	Approved
0.6468	Remote Similarity	NPD53	Approved
0.6468	Remote Similarity	NPD7778	Approved
0.6463	Remote Similarity	NPD2610	Approved
0.6463	Remote Similarity	NPD4217	Approved
0.6463	Remote Similarity	NPD3131	Approved
0.6463	Remote Similarity	NPD4218	Approved
0.6463	Remote Similarity	NPD2612	Approved
0.6463	Remote Similarity	NPD4215	Approved
0.6463	Remote Similarity	NPD2609	Approved
0.6463	Remote Similarity	NPD3132	Approved
0.6463	Remote Similarity	NPD4216	Approved
0.6463	Remote Similarity	NPD2608	Approved
0.6463	Remote Similarity	NPD2611	Approved
0.6462	Remote Similarity	NPD5444	Phase 1
0.6458	Remote Similarity	NPD3227	Phase 2
0.6453	Remote Similarity	NPD8172	Phase 2
0.6453	Remote Similarity	NPD6238	Discontinued
0.6453	Remote Similarity	NPD8173	Phase 2
0.6447	Remote Similarity	NPD2564	Approved
0.6447	Remote Similarity	NPD2565	Phase 2
0.6441	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD8423	Phase 2
0.6425	Remote Similarity	NPD8399	Phase 1
0.642	Remote Similarity	NPD5024	Approved
0.6418	Remote Similarity	NPD6206	Phase 1
0.6417	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4508	Discontinued
0.6408	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6805	Discontinued
0.64	Remote Similarity	NPD2093	Discontinued
0.6391	Remote Similarity	NPD2613	Approved
0.6384	Remote Similarity	NPD2387	Approved
0.6384	Remote Similarity	NPD3016	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7570	Approved
0.6382	Remote Similarity	NPD7569	Approved
0.6381	Remote Similarity	NPD7605	Discovery
0.6378	Remote Similarity	NPD2511	Approved
0.6368	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6999	Discontinued
0.6355	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD1036	Approved
0.6347	Remote Similarity	NPD6325	Discontinued
0.6346	Remote Similarity	NPD2509	Approved
0.6346	Remote Similarity	NPD2510	Approved
0.6345	Remote Similarity	NPD6891	Phase 2
0.6337	Remote Similarity	NPD8416	Discontinued
0.6333	Remote Similarity	NPD7528	Approved
0.6332	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD2584	Suspended
0.6324	Remote Similarity	NPD5427	Suspended
0.6324	Remote Similarity	NPD4500	Approved
0.6324	Remote Similarity	NPD4501	Approved
0.6322	Remote Similarity	NPD2670	Approved
0.6316	Remote Similarity	NPD3824	Phase 1
0.6313	Remote Similarity	NPD7234	Approved
0.6313	Remote Similarity	NPD7233	Approved
0.6313	Remote Similarity	NPD6416	Phase 2
0.6307	Remote Similarity	NPD4152	Approved
0.6305	Remote Similarity	NPD4397	Phase 1
0.6304	Remote Similarity	NPD6913	Approved
0.6301	Remote Similarity	NPD8643	Discontinued
0.63	Remote Similarity	NPD4315	Phase 2
0.6292	Remote Similarity	NPD7487	Discontinued
0.6289	Remote Similarity	NPD5897	Approved
0.6289	Remote Similarity	NPD5898	Approved
0.6289	Remote Similarity	NPD5899	Approved
0.628	Remote Similarity	NPD5426	Phase 3
0.628	Remote Similarity	NPD5981	Approved
0.628	Remote Similarity	NPD3947	Discontinued
0.6279	Remote Similarity	NPD2571	Approved
0.6279	Remote Similarity	NPD3090	Approved
0.6279	Remote Similarity	NPD3089	Approved
0.6279	Remote Similarity	NPD4746	Phase 3
0.6279	Remote Similarity	NPD2570	Approved
0.6279	Remote Similarity	NPD3088	Approved
0.6279	Remote Similarity	NPD3087	Approved
0.6279	Remote Similarity	NPD2566	Approved
0.6279	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3614	Approved
0.6279	Remote Similarity	NPD4745	Approved
0.6279	Remote Similarity	NPD2574	Discontinued
0.6279	Remote Similarity	NPD2573	Approved
0.6279	Remote Similarity	NPD3615	Approved
0.6279	Remote Similarity	NPD3616	Approved
0.6275	Remote Similarity	NPD6248	Phase 2
0.6275	Remote Similarity	NPD6249	Phase 2
0.6272	Remote Similarity	NPD7921	Approved
0.6272	Remote Similarity	NPD5993	Phase 1
0.627	Remote Similarity	NPD7011	Discontinued
0.6269	Remote Similarity	NPD6642	Approved
0.6269	Remote Similarity	NPD6641	Approved
0.6267	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5982	Phase 2
0.6264	Remote Similarity	NPD7606	Phase 3
0.6263	Remote Similarity	NPD7795	Phase 2
0.6262	Remote Similarity	NPD8326	Phase 3
0.6262	Remote Similarity	NPD8325	Phase 3
0.6262	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2607	Approved
0.625	Remote Similarity	NPD3437	Discontinued
0.6244	Remote Similarity	NPD4897	Phase 2
0.6238	Remote Similarity	NPD5947	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7944	Discontinued
0.6233	Remote Similarity	NPD7878	Phase 2
0.6232	Remote Similarity	NPD5487	Phase 1
0.623	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD2567	Approved
0.6229	Remote Similarity	NPD2569	Approved
0.6226	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD6261	Phase 3
0.6222	Remote Similarity	NPD4607	Approved
0.6222	Remote Similarity	NPD4041	Approved
0.6215	Remote Similarity	NPD3625	Discontinued
0.6207	Remote Similarity	NPD4685	Phase 3
0.6207	Remote Similarity	NPD4684	Phase 3
0.6207	Remote Similarity	NPD4686	Approved
0.6204	Remote Similarity	NPD6770	Approved
0.6202	Remote Similarity	NPD56	Approved
0.6202	Remote Similarity	NPD8282	Approved
0.6202	Remote Similarity	NPD8098	Approved
0.6202	Remote Similarity	NPD8283	Approved
0.6195	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6874	Approved
0.6193	Remote Similarity	NPD2096	Phase 2
0.6193	Remote Similarity	NPD2091	Phase 2
0.6193	Remote Similarity	NPD3436	Approved
0.6188	Remote Similarity	NPD7478	Approved
0.6188	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7869	Discontinued
0.6183	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD2210	Approved
0.6182	Remote Similarity	NPD2212	Approved
0.6179	Remote Similarity	NPD7470	Discontinued
0.6173	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD4952	Phase 3
0.6169	Remote Similarity	NPD6659	Phase 2
0.6168	Remote Similarity	NPD4176	Approved
0.6168	Remote Similarity	NPD4178	Approved
0.6168	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD3912	Discontinued
0.6164	Remote Similarity	NPD1752	Approved
0.6164	Remote Similarity	NPD1756	Approved
0.6162	Remote Similarity	NPD7072	Phase 2
0.6161	Remote Similarity	NPD4520	Approved
0.6158	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD989	Approved
0.6154	Remote Similarity	NPD979	Approved
0.6154	Remote Similarity	NPD3777	Phase 3
0.6154	Remote Similarity	NPD7205	Discontinued
0.6154	Remote Similarity	NPD2920	Discontinued
0.6154	Remote Similarity	NPD5556	Clinical (unspecified phase)

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