NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	121.03
Volume:	126.788
LogP:	0.078
LogD:	-1.318
LogS:	0.604
# Rotatable Bonds:	1
TPSA:	40.13
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	2.215
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.349
MDCK Permeability:	3.848554115393199e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.608
Plasma Protein Binding (PPB):	79.701904296875%
Volume Distribution (VD):	0.292
Pgp-substrate:	13.685354232788086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.313
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	4.045
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.859
Drug-inuced Liver Injury (DILI):	0.474
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.387
Carcinogencity:	0.072
Eye Corrosion:	0.537
Eye Irritation:	0.995
Respiratory Toxicity:	0.123

Download Data

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

Natural Product: NPC318107

Natural Product ID:	NPC318107
*Common Name:**	Sodium Benzoate
IUPAC Name:	sodium;benzoate
Synonyms:	Amzoate; E211; Mthwsh; Sodium benzoate
Standard InCHIKey:	WXMKPNITSTVMEF-UHFFFAOYSA-M
Standard InCHI:	InChI=1S/C7H6O2.Na/c8-7(9)6-4-2-1-3-5-6;/h1-5H,(H,8,9);/q;+1/p-1
SMILES:	[O-]C(=O)c1ccccc1.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1356
PubChem CID:	517055
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002565] Benzoic acids

*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
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20581114]
NPO30470	Stachylidium	Genus	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21162532]
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	roots	Whitessence Srl, Viterbo, Italy	2005-OCT	PMID[21954959]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	inflorescence	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	Kego Nature Reserve, Hatinh Province, Vietnam	2008-DEC	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	twig	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	aerial parts	Kego Nature Reserve, Hatinh Province, Vietnam	2008-DEC	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	stem	n.a.	PMID[21973101]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25515814]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	DingXi, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	LanZhou, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18212	Rhododendron ferrugineum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2846	Piper sarmentosum	Species	Piperaceae	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
Ki	8
Others	2
Potency	4

Activity Type	# Activity
Individual Protein	7
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	30000.0	nM	PMID[469782]
NPT1062	Individual Protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	74700.0	nM	PMID[469782]
NPT1143	Individual Protein	Carbonic anhydrase VA	Homo sapiens	Ki	=	7010000.0	nM	PMID[469782]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	30000.0	nM	PMID[469783]
NPT1148	Individual Protein	Carbonic anhydrase	Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Ki	=	24400.0	nM	PMID[469783]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	>	150000000.0	nM	PMID[469782]
NPT2	Others	Unspecified		Ki	=	1267000.0	nM	PMID[469783]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	730000.0	nM	PMID[469785]
NPT2	Others	Unspecified		Ratio Ki	=	0.02	n.a.	PMID[469785]
NPT2	Others	Unspecified		Ratio Ki	=	1.23	n.a.	PMID[469785]
NPT2	Others	Unspecified		Potency	n.a.	1368.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	776.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set

☑ 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 NPC318107 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	449
0.1-0.2	2456
0.2-0.3	6058
0.3-0.4	13050
0.4-0.5	11554
0.5-0.6	7365
0.6-0.7	1458
0.7-0.8	258
0.8-0.85	28
0.85-0.9	17
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC62765
0.9195	High Similarity	NPC261181
0.9091	High Similarity	NPC130398
0.8989	High Similarity	NPC61944
0.8889	High Similarity	NPC92754
0.8889	High Similarity	NPC249912
0.8889	High Similarity	NPC253423
0.8889	High Similarity	NPC276775
0.8791	High Similarity	NPC229242
0.8791	High Similarity	NPC78701
0.8791	High Similarity	NPC225060
0.8791	High Similarity	NPC35448
0.8696	High Similarity	NPC118343
0.8696	High Similarity	NPC203925
0.8696	High Similarity	NPC325497
0.8696	High Similarity	NPC228435
0.8696	High Similarity	NPC146351
0.8696	High Similarity	NPC217621
0.8602	High Similarity	NPC282895
0.8602	High Similarity	NPC42211
0.8602	High Similarity	NPC70624
0.8539	High Similarity	NPC110704
0.8511	High Similarity	NPC25458
0.8511	High Similarity	NPC304873
0.8511	High Similarity	NPC284477
0.8511	High Similarity	NPC45613
0.8511	High Similarity	NPC188895
0.8421	Intermediate Similarity	NPC89886
0.8421	Intermediate Similarity	NPC291426
0.8421	Intermediate Similarity	NPC255676
0.8421	Intermediate Similarity	NPC474365
0.8421	Intermediate Similarity	NPC60679
0.8421	Intermediate Similarity	NPC301943
0.8333	Intermediate Similarity	NPC324786
0.8333	Intermediate Similarity	NPC114594
0.8333	Intermediate Similarity	NPC31786
0.8256	Intermediate Similarity	NPC285773
0.8256	Intermediate Similarity	NPC288903
0.8247	Intermediate Similarity	NPC105899
0.8247	Intermediate Similarity	NPC269457
0.8247	Intermediate Similarity	NPC209632
0.8163	Intermediate Similarity	NPC119271
0.8163	Intermediate Similarity	NPC184658
0.8163	Intermediate Similarity	NPC30594
0.8163	Intermediate Similarity	NPC187913
0.8163	Intermediate Similarity	NPC37622
0.8111	Intermediate Similarity	NPC173443
0.8081	Intermediate Similarity	NPC56493
0.8081	Intermediate Similarity	NPC29883
0.8081	Intermediate Similarity	NPC249811
0.8068	Intermediate Similarity	NPC294134
0.8	Intermediate Similarity	NPC265407
0.8	Intermediate Similarity	NPC85493
0.8	Intermediate Similarity	NPC269023
0.8	Intermediate Similarity	NPC318327
0.8	Intermediate Similarity	NPC469636
0.8	Intermediate Similarity	NPC10251
0.8	Intermediate Similarity	NPC474364
0.8	Intermediate Similarity	NPC100551
0.8	Intermediate Similarity	NPC83628
0.8	Intermediate Similarity	NPC17417
0.8	Intermediate Similarity	NPC99846
0.7921	Intermediate Similarity	NPC216122
0.7921	Intermediate Similarity	NPC251854
0.7921	Intermediate Similarity	NPC174099
0.7921	Intermediate Similarity	NPC196246
0.7921	Intermediate Similarity	NPC214067
0.7921	Intermediate Similarity	NPC93084
0.7907	Intermediate Similarity	NPC127343
0.7895	Intermediate Similarity	NPC270654
0.7889	Intermediate Similarity	NPC89377
0.7889	Intermediate Similarity	NPC322387
0.7857	Intermediate Similarity	NPC78500
0.7843	Intermediate Similarity	NPC210089
0.7843	Intermediate Similarity	NPC474157
0.7843	Intermediate Similarity	NPC305912
0.7843	Intermediate Similarity	NPC476003
0.7843	Intermediate Similarity	NPC260818
0.7843	Intermediate Similarity	NPC243355
0.7843	Intermediate Similarity	NPC1082
0.7843	Intermediate Similarity	NPC167504
0.7835	Intermediate Similarity	NPC473325
0.7812	Intermediate Similarity	NPC160548
0.7812	Intermediate Similarity	NPC175852
0.7812	Intermediate Similarity	NPC210529
0.7802	Intermediate Similarity	NPC329064
0.7791	Intermediate Similarity	NPC300205
0.7778	Intermediate Similarity	NPC249067
0.7767	Intermediate Similarity	NPC158282
0.7767	Intermediate Similarity	NPC82899
0.7767	Intermediate Similarity	NPC66208
0.7767	Intermediate Similarity	NPC474314
0.7767	Intermediate Similarity	NPC321852
0.7767	Intermediate Similarity	NPC79496
0.7767	Intermediate Similarity	NPC270699
0.7765	Intermediate Similarity	NPC245966
0.7742	Intermediate Similarity	NPC119631
0.7717	Intermediate Similarity	NPC9822
0.7717	Intermediate Similarity	NPC220893
0.7701	Intermediate Similarity	NPC164086
0.7692	Intermediate Similarity	NPC474176
0.7692	Intermediate Similarity	NPC161611
0.7692	Intermediate Similarity	NPC272524
0.7692	Intermediate Similarity	NPC128368
0.7677	Intermediate Similarity	NPC329556
0.7674	Intermediate Similarity	NPC2785
0.7674	Intermediate Similarity	NPC36342
0.7674	Intermediate Similarity	NPC285470
0.7667	Intermediate Similarity	NPC58616
0.7667	Intermediate Similarity	NPC95965
0.7653	Intermediate Similarity	NPC52472
0.764	Intermediate Similarity	NPC44830
0.7634	Intermediate Similarity	NPC86670
0.7634	Intermediate Similarity	NPC70940
0.7634	Intermediate Similarity	NPC274455
0.7619	Intermediate Similarity	NPC237366
0.7619	Intermediate Similarity	NPC474363
0.7619	Intermediate Similarity	NPC307651
0.7619	Intermediate Similarity	NPC153053
0.7619	Intermediate Similarity	NPC211421
0.7619	Intermediate Similarity	NPC308744
0.7614	Intermediate Similarity	NPC73978
0.7556	Intermediate Similarity	NPC44546
0.7551	Intermediate Similarity	NPC245561
0.7549	Intermediate Similarity	NPC226699
0.7549	Intermediate Similarity	NPC34715
0.7549	Intermediate Similarity	NPC141523
0.7549	Intermediate Similarity	NPC211439
0.7549	Intermediate Similarity	NPC303264
0.7547	Intermediate Similarity	NPC81808
0.7547	Intermediate Similarity	NPC186933
0.7547	Intermediate Similarity	NPC306740
0.7547	Intermediate Similarity	NPC210092
0.7547	Intermediate Similarity	NPC474685
0.7529	Intermediate Similarity	NPC206800
0.7529	Intermediate Similarity	NPC32203
0.7528	Intermediate Similarity	NPC323103
0.7526	Intermediate Similarity	NPC156021
0.7525	Intermediate Similarity	NPC163734
0.7525	Intermediate Similarity	NPC219913
0.75	Intermediate Similarity	NPC121800
0.75	Intermediate Similarity	NPC71664
0.75	Intermediate Similarity	NPC160382
0.75	Intermediate Similarity	NPC190567
0.75	Intermediate Similarity	NPC13426
0.7477	Intermediate Similarity	NPC220540
0.7477	Intermediate Similarity	NPC100353
0.7477	Intermediate Similarity	NPC188907
0.7477	Intermediate Similarity	NPC149691
0.7476	Intermediate Similarity	NPC224584
0.7453	Intermediate Similarity	NPC98543
0.7453	Intermediate Similarity	NPC223004
0.7451	Intermediate Similarity	NPC6984
0.7447	Intermediate Similarity	NPC213156
0.7447	Intermediate Similarity	NPC240108
0.7444	Intermediate Similarity	NPC270507
0.7444	Intermediate Similarity	NPC215008
0.7444	Intermediate Similarity	NPC273758
0.7426	Intermediate Similarity	NPC269644
0.7423	Intermediate Similarity	NPC246679
0.7419	Intermediate Similarity	NPC304760
0.7416	Intermediate Similarity	NPC100039
0.7416	Intermediate Similarity	NPC12936
0.7416	Intermediate Similarity	NPC273033
0.7416	Intermediate Similarity	NPC145053
0.7407	Intermediate Similarity	NPC312800
0.7407	Intermediate Similarity	NPC131192
0.7407	Intermediate Similarity	NPC128825
0.7407	Intermediate Similarity	NPC158157
0.7404	Intermediate Similarity	NPC95172
0.74	Intermediate Similarity	NPC320891
0.7386	Intermediate Similarity	NPC170484
0.7383	Intermediate Similarity	NPC476357
0.7368	Intermediate Similarity	NPC317645
0.7356	Intermediate Similarity	NPC3672
0.7356	Intermediate Similarity	NPC287790
0.7353	Intermediate Similarity	NPC13495
0.7347	Intermediate Similarity	NPC289201
0.7339	Intermediate Similarity	NPC45104
0.7339	Intermediate Similarity	NPC469574
0.7339	Intermediate Similarity	NPC160199
0.7339	Intermediate Similarity	NPC240664
0.7339	Intermediate Similarity	NPC217423
0.7339	Intermediate Similarity	NPC228318
0.7333	Intermediate Similarity	NPC103387
0.7333	Intermediate Similarity	NPC474057
0.732	Intermediate Similarity	NPC32977
0.732	Intermediate Similarity	NPC81010
0.732	Intermediate Similarity	NPC172925
0.7312	Intermediate Similarity	NPC194326
0.7308	Intermediate Similarity	NPC17525
0.73	Intermediate Similarity	NPC112552
0.7292	Intermediate Similarity	NPC77273
0.7282	Intermediate Similarity	NPC1065
0.7282	Intermediate Similarity	NPC317592
0.7273	Intermediate Similarity	NPC273282
0.7273	Intermediate Similarity	NPC474890
0.7273	Intermediate Similarity	NPC176228
0.7273	Intermediate Similarity	NPC94637
0.7273	Intermediate Similarity	NPC161943

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 NPC318107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	947
0.2-0.3	1650
0.3-0.4	3131
0.4-0.5	1999
0.5-0.6	790
0.6-0.7	158
0.7-0.8	50
0.8-0.85	6
0.85-0.9	3
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD9257	Approved
1.0	High Similarity	NPD9259	Approved
0.9524	High Similarity	NPD9256	Approved
0.9524	High Similarity	NPD9258	Approved
0.9195	High Similarity	NPD1202	Approved
0.9091	High Similarity	NPD9260	Approved
0.8696	High Similarity	NPD1238	Approved
0.8659	High Similarity	NPD9490	Approved
0.8421	Intermediate Similarity	NPD9261	Approved
0.8333	Intermediate Similarity	NPD164	Approved
0.8256	Intermediate Similarity	NPD9491	Approved
0.8095	Intermediate Similarity	NPD227	Approved
0.8095	Intermediate Similarity	NPD225	Approved
0.8081	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD9263	Approved
0.8081	Intermediate Similarity	NPD9267	Approved
0.8081	Intermediate Similarity	NPD9264	Approved
0.8	Intermediate Similarity	NPD74	Approved
0.8	Intermediate Similarity	NPD9266	Approved
0.8	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2182	Approved
0.7889	Intermediate Similarity	NPD1087	Approved
0.7843	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD226	Approved
0.7812	Intermediate Similarity	NPD9495	Approved
0.7778	Intermediate Similarity	NPD1237	Approved
0.7767	Intermediate Similarity	NPD9508	Approved
0.7717	Intermediate Similarity	NPD800	Approved
0.7692	Intermediate Similarity	NPD5277	Phase 2
0.7677	Intermediate Similarity	NPD1930	Approved
0.7677	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1929	Approved
0.7634	Intermediate Similarity	NPD1089	Approved
0.7634	Intermediate Similarity	NPD1086	Approved
0.7634	Intermediate Similarity	NPD1090	Approved
0.7553	Intermediate Similarity	NPD1239	Approved
0.7551	Intermediate Similarity	NPD2066	Phase 3
0.7547	Intermediate Similarity	NPD9281	Approved
0.7547	Intermediate Similarity	NPD5951	Approved
0.7529	Intermediate Similarity	NPD9716	Approved
0.7474	Intermediate Similarity	NPD1088	Approved
0.7416	Intermediate Similarity	NPD942	Approved
0.7407	Intermediate Similarity	NPD9493	Approved
0.74	Intermediate Similarity	NPD1932	Approved
0.7396	Intermediate Similarity	NPD1563	Approved
0.732	Intermediate Similarity	NPD1693	Approved
0.732	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4793	Discontinued
0.7273	Intermediate Similarity	NPD9545	Approved
0.7264	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD1989	Approved
0.7222	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1565	Approved
0.7172	Intermediate Similarity	NPD1566	Phase 3
0.7172	Intermediate Similarity	NPD1564	Approved
0.7159	Intermediate Similarity	NPD9294	Approved
0.7158	Intermediate Similarity	NPD5347	Phase 2
0.7158	Intermediate Similarity	NPD5346	Phase 2
0.7143	Intermediate Similarity	NPD1104	Approved
0.7143	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9272	Approved
0.7143	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD650	Approved
0.7083	Intermediate Similarity	NPD3673	Approved
0.7083	Intermediate Similarity	NPD3672	Approved
0.708	Intermediate Similarity	NPD1889	Phase 1
0.7033	Intermediate Similarity	NPD9250	Approved
0.7018	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6287	Discontinued
0.6981	Remote Similarity	NPD2329	Discontinued
0.6957	Remote Similarity	NPD9717	Approved
0.6947	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5909	Discontinued
0.6916	Remote Similarity	NPD1317	Discontinued
0.6916	Remote Similarity	NPD2067	Discontinued
0.6909	Remote Similarity	NPD1246	Approved
0.6903	Remote Similarity	NPD9268	Approved
0.6897	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD9697	Approved
0.6838	Remote Similarity	NPD2198	Approved
0.6838	Remote Similarity	NPD2199	Approved
0.6838	Remote Similarity	NPD1888	Phase 1
0.6837	Remote Similarity	NPD7609	Phase 3
0.6827	Remote Similarity	NPD6647	Phase 2
0.6818	Remote Similarity	NPD1241	Discontinued
0.681	Remote Similarity	NPD9269	Phase 2
0.678	Remote Similarity	NPD552	Approved
0.678	Remote Similarity	NPD1164	Approved
0.678	Remote Similarity	NPD9567	Approved
0.678	Remote Similarity	NPD553	Approved
0.678	Remote Similarity	NPD1203	Approved
0.6771	Remote Similarity	NPD1282	Approved
0.6768	Remote Similarity	NPD7631	Approved
0.6768	Remote Similarity	NPD1508	Approved
0.6765	Remote Similarity	NPD9710	Approved
0.6765	Remote Similarity	NPD9711	Approved
0.6757	Remote Similarity	NPD2629	Approved
0.6733	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1019	Discontinued
0.6702	Remote Similarity	NPD3971	Phase 1
0.6699	Remote Similarity	NPD9712	Approved
0.6667	Remote Similarity	NPD9566	Approved
0.6638	Remote Similarity	NPD9693	Approved
0.6638	Remote Similarity	NPD9692	Approved
0.6636	Remote Similarity	NPD3134	Approved
0.6612	Remote Similarity	NPD6832	Phase 2
0.6609	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1245	Approved
0.6602	Remote Similarity	NPD253	Approved
0.6581	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2347	Approved
0.6574	Remote Similarity	NPD1358	Approved
0.6569	Remote Similarity	NPD1843	Approved
0.6562	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7008	Discontinued
0.6557	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6966	Discovery
0.6552	Remote Similarity	NPD2345	Approved
0.6549	Remote Similarity	NPD255	Approved
0.6549	Remote Similarity	NPD256	Approved
0.6538	Remote Similarity	NPD7798	Approved
0.6538	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD3972	Approved
0.6525	Remote Similarity	NPD4878	Approved
0.6509	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD3495	Discontinued
0.6504	Remote Similarity	NPD3764	Approved
0.6504	Remote Similarity	NPD2313	Discontinued
0.6504	Remote Similarity	NPD411	Approved
0.6491	Remote Similarity	NPD9568	Approved
0.6471	Remote Similarity	NPD5157	Phase 1
0.6471	Remote Similarity	NPD5159	Phase 2
0.6471	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4102	Approved
0.6466	Remote Similarity	NPD4105	Approved
0.6465	Remote Similarity	NPD9249	Phase 1
0.6465	Remote Similarity	NPD689	Discontinued
0.6455	Remote Similarity	NPD1756	Approved
0.6455	Remote Similarity	NPD1752	Approved
0.6455	Remote Similarity	NPD4234	Approved
0.6455	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4233	Approved
0.6452	Remote Similarity	NPD520	Approved
0.6446	Remote Similarity	NPD2798	Approved
0.6442	Remote Similarity	NPD5926	Approved
0.6441	Remote Similarity	NPD1201	Approved
0.6435	Remote Similarity	NPD1758	Phase 1
0.6417	Remote Similarity	NPD1876	Approved
0.641	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5306	Approved
0.641	Remote Similarity	NPD5305	Approved
0.641	Remote Similarity	NPD17	Approved
0.64	Remote Similarity	NPD3373	Approved
0.64	Remote Similarity	NPD4307	Phase 2
0.6396	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD111	Approved
0.6379	Remote Similarity	NPD1759	Phase 1
0.6379	Remote Similarity	NPD1894	Discontinued
0.6373	Remote Similarity	NPD1066	Discontinued
0.6371	Remote Similarity	NPD9471	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1470	Approved
0.6356	Remote Similarity	NPD4135	Approved
0.6356	Remote Similarity	NPD4106	Approved
0.6356	Remote Similarity	NPD4136	Approved
0.6349	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD447	Suspended
0.6349	Remote Similarity	NPD1933	Approved
0.6346	Remote Similarity	NPD1099	Approved
0.6346	Remote Similarity	NPD1100	Approved
0.6339	Remote Similarity	NPD969	Suspended
0.6311	Remote Similarity	NPD4980	Approved
0.6306	Remote Similarity	NPD5235	Approved
0.6306	Remote Similarity	NPD5236	Approved
0.6306	Remote Similarity	NPD5239	Approved
0.6306	Remote Similarity	NPD5240	Approved
0.6306	Remote Similarity	NPD5237	Approved
0.6303	Remote Similarity	NPD4806	Approved
0.6303	Remote Similarity	NPD1281	Approved
0.6303	Remote Similarity	NPD4807	Approved
0.6299	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD2607	Approved
0.6283	Remote Similarity	NPD181	Approved
0.6281	Remote Similarity	NPD1574	Approved
0.6275	Remote Similarity	NPD159	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2201	Approved
0.625	Remote Similarity	NPD2670	Approved
0.625	Remote Similarity	NPD1481	Phase 2
0.625	Remote Similarity	NPD2569	Approved
0.625	Remote Similarity	NPD2567	Approved
0.625	Remote Similarity	NPD9279	Approved
0.625	Remote Similarity	NPD1608	Approved
0.6239	Remote Similarity	NPD5048	Discontinued
0.6239	Remote Similarity	NPD1040	Phase 2
0.623	Remote Similarity	NPD2797	Approved
0.623	Remote Similarity	NPD3267	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