NPASS Compound

Structure

NPC245741 OpenBabel07101719122D 26 30 0 0 1 0 0 0 0 0999 V2000 5.4189 -3.3432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4273 -3.4728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0130 -0.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4401 -1.7536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6480 -0.7754 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0129 -0.0030 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8193 -2.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5457 -2.2009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6383 -1.7805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4401 -1.7536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6436 -1.5737 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 2.5607 -3.2008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4310 -1.8878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5457 -2.2009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 25 1 0 0 0 0 3 14 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 2 0 0 0 0 7 13 2 0 0 0 0 9 26 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 9 1 1 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 8 1 1 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 0 0 0 0 15 19 1 1 0 0 0 15 22 1 0 0 0 0 16 18 1 1 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 17 23 2 0 0 0 0 18 8 1 1 0 0 0 19 24 1 1 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.15
Volume:	347.16
LogP:	1.724
LogD:	1.587
LogS:	-4.126
# Rotatable Bonds:	2
TPSA:	91.59
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.807
Synthetic Accessibility Score:	6.483
Fsp3:	0.579
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:	-4.99
MDCK Permeability:	4.736015762318857e-05
Pgp-inhibitor:	0.232
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.114

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817
Plasma Protein Binding (PPB):	48.77880096435547%
Volume Distribution (VD):	0.957
Pgp-substrate:	27.801498413085938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.89

ADMET: Excretion

Clearance (CL):	7.422
Half-life (T1/2):	0.039

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.188
AMES Toxicity:	0.89
Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.817
Skin Sensitization:	0.487
Carcinogencity:	0.927
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC245741

Natural Product ID:	NPC245741
*Common Name:**	HVRXIIBZQVCBAF-UGHGSSRZSA-N
IUPAC Name:	n.a.
Synonyms:	14,15-Dihydroxygelsenicine
Standard InCHIKey:	HVRXIIBZQVCBAF-UGHGSSRZSA-N
Standard InCHI:	InChI=1S/C19H22N2O5/c1-3-14-19(24)11-9-26-16(15(19)22)18(8-12(11)20-14)10-6-4-5-7-13(10)21(25-2)17(18)23/h4-7,11-12,15-16,22,24H,3,8-9H2,1-2H3/t11-,12+,15+,16-,18+,19+/m1/s1
SMILES:	CON1c2ccccc2[C@@]2(C1=O)C[C@@H]1N=C([C@@]3([C@H]([C@H]2OC[C@H]13)O)O)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL527011
PubChem CID:	44583829
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	=	1300.0	nM	PMID[450348]

☑ 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 NPC245741 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	248
0.1-0.2	1170
0.2-0.3	4128
0.3-0.4	17203
0.4-0.5	15452
0.5-0.6	4007
0.6-0.7	459
0.7-0.8	17
0.8-0.85	5
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC282092
0.9217	High Similarity	NPC13367
0.9018	High Similarity	NPC143457
0.8933	High Similarity	NPC302548
0.8933	High Similarity	NPC475559
0.8678	High Similarity	NPC477159
0.8495	Intermediate Similarity	NPC14339
0.8274	Intermediate Similarity	NPC29285
0.8232	Intermediate Similarity	NPC284706
0.8187	Intermediate Similarity	NPC286871
0.7977	Intermediate Similarity	NPC176983
0.7877	Intermediate Similarity	NPC129624
0.7584	Intermediate Similarity	NPC472106
0.7514	Intermediate Similarity	NPC475962
0.7472	Intermediate Similarity	NPC472101
0.7472	Intermediate Similarity	NPC472120
0.7416	Intermediate Similarity	NPC309531
0.7416	Intermediate Similarity	NPC472102
0.7401	Intermediate Similarity	NPC153694
0.7401	Intermediate Similarity	NPC211525
0.74	Intermediate Similarity	NPC477160
0.7377	Intermediate Similarity	NPC210415
0.7377	Intermediate Similarity	NPC298851
0.7377	Intermediate Similarity	NPC293255
0.7377	Intermediate Similarity	NPC181138
0.7377	Intermediate Similarity	NPC21752
0.7377	Intermediate Similarity	NPC276993
0.7374	Intermediate Similarity	NPC472117
0.7374	Intermediate Similarity	NPC472121
0.736	Intermediate Similarity	NPC310403
0.736	Intermediate Similarity	NPC263709
0.736	Intermediate Similarity	NPC97380
0.736	Intermediate Similarity	NPC243673
0.736	Intermediate Similarity	NPC148468
0.736	Intermediate Similarity	NPC63210
0.7348	Intermediate Similarity	NPC278887
0.7303	Intermediate Similarity	NPC113946
0.7293	Intermediate Similarity	NPC52059
0.7293	Intermediate Similarity	NPC470069
0.7283	Intermediate Similarity	NPC472100
0.7268	Intermediate Similarity	NPC243626
0.7267	Intermediate Similarity	NPC472103
0.7259	Intermediate Similarity	NPC475489
0.7211	Intermediate Similarity	NPC472209
0.7204	Intermediate Similarity	NPC476441
0.7191	Intermediate Similarity	NPC161827
0.7189	Intermediate Similarity	NPC96901
0.7179	Intermediate Similarity	NPC230313
0.7165	Intermediate Similarity	NPC473004
0.7143	Intermediate Similarity	NPC476428
0.7143	Intermediate Similarity	NPC313757
0.7127	Intermediate Similarity	NPC315368
0.712	Intermediate Similarity	NPC469460
0.712	Intermediate Similarity	NPC469462
0.7097	Intermediate Similarity	NPC476425
0.7083	Intermediate Similarity	NPC291759
0.705	Intermediate Similarity	NPC471512
0.7031	Intermediate Similarity	NPC133591
0.7005	Intermediate Similarity	NPC221687
0.7	Intermediate Similarity	NPC11149
0.6995	Remote Similarity	NPC477161
0.6995	Remote Similarity	NPC476231
0.6995	Remote Similarity	NPC38823
0.6995	Remote Similarity	NPC207033
0.6984	Remote Similarity	NPC476326
0.6976	Remote Similarity	NPC469743
0.6974	Remote Similarity	NPC473008
0.6974	Remote Similarity	NPC22689
0.6974	Remote Similarity	NPC105055
0.6973	Remote Similarity	NPC214960
0.6973	Remote Similarity	NPC279527
0.697	Remote Similarity	NPC97100
0.697	Remote Similarity	NPC473375
0.6957	Remote Similarity	NPC475778
0.694	Remote Similarity	NPC474058
0.6936	Remote Similarity	NPC243162
0.6935	Remote Similarity	NPC90967
0.6915	Remote Similarity	NPC139085
0.6915	Remote Similarity	NPC251212
0.6915	Remote Similarity	NPC214626
0.6912	Remote Similarity	NPC277350
0.6911	Remote Similarity	NPC39822
0.6906	Remote Similarity	NPC473297
0.69	Remote Similarity	NPC149708
0.6895	Remote Similarity	NPC260075
0.6868	Remote Similarity	NPC477157
0.6868	Remote Similarity	NPC477156
0.686	Remote Similarity	NPC234999
0.6859	Remote Similarity	NPC475094
0.6847	Remote Similarity	NPC474077
0.6839	Remote Similarity	NPC315051
0.6832	Remote Similarity	NPC214428
0.6809	Remote Similarity	NPC469915
0.6793	Remote Similarity	NPC469461
0.6786	Remote Similarity	NPC473815
0.6772	Remote Similarity	NPC355
0.6771	Remote Similarity	NPC321211
0.6769	Remote Similarity	NPC473007
0.6769	Remote Similarity	NPC52262
0.6769	Remote Similarity	NPC62510
0.6757	Remote Similarity	NPC477158
0.6757	Remote Similarity	NPC201424
0.6749	Remote Similarity	NPC470497
0.6738	Remote Similarity	NPC471124
0.6736	Remote Similarity	NPC15840
0.6735	Remote Similarity	NPC478077
0.6734	Remote Similarity	NPC204970
0.672	Remote Similarity	NPC85651
0.6717	Remote Similarity	NPC473298
0.6714	Remote Similarity	NPC151976
0.6701	Remote Similarity	NPC472323
0.67	Remote Similarity	NPC203972
0.6699	Remote Similarity	NPC475847
0.6699	Remote Similarity	NPC185742
0.6698	Remote Similarity	NPC204491
0.6684	Remote Similarity	NPC79062
0.6684	Remote Similarity	NPC218594
0.6684	Remote Similarity	NPC99043
0.6684	Remote Similarity	NPC472107
0.6684	Remote Similarity	NPC322621
0.6683	Remote Similarity	NPC162730
0.6683	Remote Similarity	NPC474116
0.6682	Remote Similarity	NPC473006
0.6682	Remote Similarity	NPC141428
0.6667	Remote Similarity	NPC225319
0.6667	Remote Similarity	NPC68650
0.6667	Remote Similarity	NPC474121
0.6667	Remote Similarity	NPC249428
0.6667	Remote Similarity	NPC472444
0.6651	Remote Similarity	NPC267926
0.665	Remote Similarity	NPC55493
0.6648	Remote Similarity	NPC116519
0.6647	Remote Similarity	NPC477680
0.6636	Remote Similarity	NPC266192
0.6633	Remote Similarity	NPC472119
0.6633	Remote Similarity	NPC97584
0.6632	Remote Similarity	NPC472118
0.6621	Remote Similarity	NPC57690
0.6618	Remote Similarity	NPC241024
0.6615	Remote Similarity	NPC472586
0.6615	Remote Similarity	NPC113626
0.6614	Remote Similarity	NPC472115
0.6614	Remote Similarity	NPC472114
0.6613	Remote Similarity	NPC471122
0.6607	Remote Similarity	NPC317758
0.6603	Remote Similarity	NPC127677
0.66	Remote Similarity	NPC25401
0.66	Remote Similarity	NPC117244
0.66	Remote Similarity	NPC473763
0.6598	Remote Similarity	NPC472443
0.6593	Remote Similarity	NPC162104
0.6584	Remote Similarity	NPC34717
0.6576	Remote Similarity	NPC478076
0.6575	Remote Similarity	NPC212799
0.6569	Remote Similarity	NPC52557
0.6569	Remote Similarity	NPC102008
0.6562	Remote Similarity	NPC285622
0.6557	Remote Similarity	NPC10732
0.6557	Remote Similarity	NPC87856
0.6555	Remote Similarity	NPC46225
0.655	Remote Similarity	NPC471195
0.655	Remote Similarity	NPC471196
0.6546	Remote Similarity	NPC186669
0.6546	Remote Similarity	NPC474081
0.6543	Remote Similarity	NPC35510
0.6543	Remote Similarity	NPC253667
0.6542	Remote Similarity	NPC203614
0.6542	Remote Similarity	NPC132211
0.6538	Remote Similarity	NPC242000
0.6534	Remote Similarity	NPC287358
0.6533	Remote Similarity	NPC181928
0.653	Remote Similarity	NPC477394
0.6526	Remote Similarity	NPC267965
0.6517	Remote Similarity	NPC28510
0.6515	Remote Similarity	NPC259626
0.6513	Remote Similarity	NPC274002
0.6513	Remote Similarity	NPC126515
0.6513	Remote Similarity	NPC475761
0.6513	Remote Similarity	NPC472331
0.6513	Remote Similarity	NPC133261
0.6512	Remote Similarity	NPC244425
0.6512	Remote Similarity	NPC15384
0.6507	Remote Similarity	NPC477173
0.6507	Remote Similarity	NPC18661
0.6505	Remote Similarity	NPC138830
0.65	Remote Similarity	NPC175474
0.6495	Remote Similarity	NPC472122
0.6495	Remote Similarity	NPC24594
0.6495	Remote Similarity	NPC203202
0.6495	Remote Similarity	NPC475607
0.6495	Remote Similarity	NPC264482
0.6488	Remote Similarity	NPC470499
0.6482	Remote Similarity	NPC262725
0.6481	Remote Similarity	NPC174788
0.6477	Remote Similarity	NPC208725
0.6476	Remote Similarity	NPC470488
0.6471	Remote Similarity	NPC473458
0.6471	Remote Similarity	NPC104345
0.6471	Remote Similarity	NPC474926
0.6468	Remote Similarity	NPC174629

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 NPC245741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	472
0.2-0.3	739
0.3-0.4	1890
0.4-0.5	3928
0.5-0.6	1853
0.6-0.7	102
0.7-0.8	0
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
0.7207	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7599	Phase 2
0.7033	Intermediate Similarity	NPD7600	Phase 2
0.6912	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1663	Discontinued
0.6816	Remote Similarity	NPD4682	Phase 2
0.6776	Remote Similarity	NPD7105	Phase 1
0.6765	Remote Similarity	NPD4738	Phase 2
0.6758	Remote Similarity	NPD4121	Phase 3
0.6758	Remote Similarity	NPD4120	Approved
0.675	Remote Similarity	NPD4427	Phase 2
0.6721	Remote Similarity	NPD5742	Approved
0.6721	Remote Similarity	NPD5743	Approved
0.6721	Remote Similarity	NPD5741	Approved
0.6601	Remote Similarity	NPD5003	Discontinued
0.6587	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7001	Phase 3
0.6578	Remote Similarity	NPD2996	Approved
0.6571	Remote Similarity	NPD8173	Phase 2
0.6571	Remote Similarity	NPD8172	Phase 2
0.6569	Remote Similarity	NPD7777	Approved
0.6569	Remote Similarity	NPD7778	Approved
0.6569	Remote Similarity	NPD53	Approved
0.6564	Remote Similarity	NPD6879	Phase 2
0.6564	Remote Similarity	NPD6878	Phase 2
0.6556	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3824	Phase 1
0.6489	Remote Similarity	NPD2511	Approved
0.648	Remote Similarity	NPD3227	Phase 2
0.6471	Remote Similarity	NPD1036	Approved
0.6468	Remote Similarity	NPD4499	Approved
0.6468	Remote Similarity	NPD2565	Phase 2
0.6468	Remote Similarity	NPD2564	Approved
0.6444	Remote Similarity	NPD2820	Phase 3
0.6435	Remote Similarity	NPD8326	Phase 3
0.6435	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD8325	Phase 3
0.6425	Remote Similarity	NPD4600	Approved
0.6425	Remote Similarity	NPD4601	Approved
0.6422	Remote Similarity	NPD4602	Approved
0.6422	Remote Similarity	NPD7944	Discontinued
0.6418	Remote Similarity	NPD4334	Discontinued
0.6417	Remote Similarity	NPD3067	Approved
0.641	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD2844	Phase 3
0.6396	Remote Similarity	NPD5897	Approved
0.6396	Remote Similarity	NPD5899	Approved
0.6396	Remote Similarity	NPD5898	Approved
0.6391	Remote Similarity	NPD4215	Approved
0.6391	Remote Similarity	NPD4218	Approved
0.6391	Remote Similarity	NPD3132	Approved
0.6391	Remote Similarity	NPD3131	Approved
0.6391	Remote Similarity	NPD4216	Approved
0.6391	Remote Similarity	NPD2610	Approved
0.6391	Remote Similarity	NPD2609	Approved
0.6391	Remote Similarity	NPD2608	Approved
0.6391	Remote Similarity	NPD4217	Approved
0.6391	Remote Similarity	NPD2612	Approved
0.6391	Remote Similarity	NPD2611	Approved
0.6389	Remote Similarity	NPD2365	Approved
0.6385	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7011	Discontinued
0.6378	Remote Similarity	NPD6641	Approved
0.6378	Remote Similarity	NPD6642	Approved
0.6377	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6999	Discontinued
0.6374	Remote Similarity	NPD6325	Discontinued
0.6359	Remote Similarity	NPD5942	Approved
0.6359	Remote Similarity	NPD5941	Approved
0.6359	Remote Similarity	NPD6206	Phase 1
0.6359	Remote Similarity	NPD4432	Discontinued
0.6358	Remote Similarity	NPD3626	Phase 3
0.6355	Remote Similarity	NPD5076	Approved
0.6355	Remote Similarity	NPD5077	Approved
0.633	Remote Similarity	NPD7878	Phase 2
0.6322	Remote Similarity	NPD2613	Approved
0.6311	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5426	Phase 3
0.6294	Remote Similarity	NPD3449	Discontinued
0.6293	Remote Similarity	NPD7921	Approved
0.6291	Remote Similarity	NPD8399	Phase 1
0.6291	Remote Similarity	NPD8423	Phase 2
0.629	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD8417	Discontinued
0.6275	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6274	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5182	Approved
0.6271	Remote Similarity	NPD5185	Approved
0.6271	Remote Similarity	NPD5184	Approved
0.627	Remote Similarity	NPD979	Approved
0.6268	Remote Similarity	NPD6805	Discontinued
0.6262	Remote Similarity	NPD5947	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7820	Phase 3
0.6256	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5596	Phase 2
0.6244	Remote Similarity	NPD4315	Phase 2
0.6243	Remote Similarity	NPD4152	Approved
0.6243	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD6395	Phase 2
0.6243	Remote Similarity	NPD6913	Approved
0.6243	Remote Similarity	NPD2093	Discontinued
0.6233	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6249	Phase 2
0.622	Remote Similarity	NPD6248	Phase 2
0.6215	Remote Similarity	NPD3088	Approved
0.6215	Remote Similarity	NPD3090	Approved
0.6215	Remote Similarity	NPD2571	Approved
0.6215	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD3089	Approved
0.6215	Remote Similarity	NPD3616	Approved
0.6215	Remote Similarity	NPD2574	Discontinued
0.6215	Remote Similarity	NPD2573	Approved
0.6215	Remote Similarity	NPD3615	Approved
0.6215	Remote Similarity	NPD2570	Approved
0.6215	Remote Similarity	NPD3087	Approved
0.6215	Remote Similarity	NPD2566	Approved
0.6215	Remote Similarity	NPD3614	Approved
0.6215	Remote Similarity	NPD4746	Phase 3
0.6215	Remote Similarity	NPD4745	Approved
0.6213	Remote Similarity	NPD2212	Approved
0.6213	Remote Similarity	NPD2210	Approved
0.6211	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6891	Phase 2
0.6204	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD2995	Approved
0.6196	Remote Similarity	NPD7295	Approved
0.6195	Remote Similarity	NPD8374	Phase 3
0.6193	Remote Similarity	NPD4897	Phase 2
0.6186	Remote Similarity	NPD5823	Approved
0.6186	Remote Similarity	NPD4506	Discontinued
0.6185	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD5578	Approved
0.6183	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.618	Remote Similarity	NPD8416	Discontinued
0.6179	Remote Similarity	NPD2920	Discontinued
0.6179	Remote Similarity	NPD5487	Phase 1
0.6179	Remote Similarity	NPD6176	Phase 1
0.6178	Remote Similarity	NPD4086	Phase 1
0.6175	Remote Similarity	NPD5024	Approved
0.6175	Remote Similarity	NPD4852	Phase 2
0.6175	Remote Similarity	NPD7605	Discovery
0.6173	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6261	Phase 3
0.6169	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7570	Approved
0.6165	Remote Similarity	NPD7569	Approved
0.6158	Remote Similarity	NPD2527	Approved
0.6158	Remote Similarity	NPD951	Approved
0.6157	Remote Similarity	NPD8329	Phase 3
0.6154	Remote Similarity	NPD6455	Phase 3
0.6154	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4684	Phase 3
0.6145	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4686	Approved
0.6145	Remote Similarity	NPD4685	Phase 3
0.6143	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD6995	Phase 1
0.6142	Remote Similarity	NPD43	Approved
0.6142	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6182	Approved
0.6141	Remote Similarity	NPD7487	Discontinued
0.6141	Remote Similarity	NPD2575	Approved
0.6141	Remote Similarity	NPD3016	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7665	Phase 2
0.614	Remote Similarity	NPD7666	Phase 3
0.6136	Remote Similarity	NPD1271	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD4951	Discontinued
0.6126	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7795	Phase 2
0.6117	Remote Similarity	NPD6659	Phase 2
0.6117	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD8240	Discontinued
0.6108	Remote Similarity	NPD8323	Discontinued
0.6108	Remote Similarity	NPD6557	Phase 2
0.6103	Remote Similarity	NPD3777	Phase 3
0.6101	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD7301	Phase 3
0.6095	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4397	Phase 1
0.6089	Remote Similarity	NPD7962	Phase 2
0.6087	Remote Similarity	NPD6301	Phase 2
0.608	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5444	Phase 1
0.6078	Remote Similarity	NPD3153	Approved
0.6078	Remote Similarity	NPD3154	Approved
0.6075	Remote Similarity	NPD3141	Discontinued
0.6075	Remote Similarity	NPD6416	Phase 2
0.6071	Remote Similarity	NPD6457	Approved
0.6069	Remote Similarity	NPD2584	Suspended
0.6068	Remote Similarity	NPD6517	Phase 3
0.6066	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6874	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