NPASS Compound

Structure

NPC99795 OpenBabel07101719242D 23 26 0 0 1 0 0 0 0 0999 V2000 2.6188 -1.4635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7739 -2.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5971 -1.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1604 -0.2806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8122 0.9321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2617 0.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1531 0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0280 -1.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5768 -1.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0283 -0.5694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7599 -1.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8869 -1.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.5120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7039 -2.0241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5908 -0.5363 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8589 -0.5121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8729 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1632 -0.2059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 -0.0242 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7319 0.0242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0140 0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0158 -1.4594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 19 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 12 17 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 9 1 6 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 20 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	338.712
LogP:	4.617
LogD:	3.526
LogS:	-3.92
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.734
Synthetic Accessibility Score:	5.304
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.655
MDCK Permeability:	1.8948590877698734e-05
Pgp-inhibitor:	0.739
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.459
Plasma Protein Binding (PPB):	98.34188079833984%
Volume Distribution (VD):	3.69
Pgp-substrate:	2.6481997966766357%

ADMET: Metabolism

CYP1A2-inhibitor:	0.189
CYP1A2-substrate:	0.846
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.302
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.297
CYP2D6-substrate:	0.552
CYP3A4-inhibitor:	0.263
CYP3A4-substrate:	0.374

ADMET: Excretion

Clearance (CL):	3.908
Half-life (T1/2):	0.325

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.363
Drug-inuced Liver Injury (DILI):	0.15
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.837
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.954
Carcinogencity:	0.233
Eye Corrosion:	0.006
Eye Irritation:	0.91
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC99795

Natural Product ID:	NPC99795
*Common Name:**	XCVWKCGUFCXDHN-AUSJPIAWSA-N
IUPAC Name:	n.a.
Synonyms:	20-Deoxocarnosol
Standard InCHIKey:	XCVWKCGUFCXDHN-AUSJPIAWSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-11(2)12-8-13-14-9-15-19(3,4)6-5-7-20(15,10-23-14)16(13)18(22)17(12)21/h8,11,14-15,21-22H,5-7,9-10H2,1-4H3/t14-,15-,20+/m0/s1
SMILES:	Oc1c(O)c(cc2c1[C@]13CCCC([C@@H]3C[C@@H]2OC1)(C)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491879
PubChem CID:	13855851
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO20067	Salvia pachyphylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190465]
NPO2794	Salvia clevelandii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190465]
NPO2794	Salvia clevelandii	Species	Lamiaceae	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
GI50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	GI50	=	5400.0	nM	PMID[473074]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	22000.0	nM	PMID[473074]
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	=	32000.0	nM	PMID[473074]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	32000.0	nM	PMID[473074]
NPT1723	Cell Line	HBL-100	Homo sapiens	GI50	=	4600.0	nM	PMID[473074]

☑ 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 NPC99795 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	419
0.1-0.2	1518
0.2-0.3	3293
0.3-0.4	7992
0.4-0.5	10686
0.5-0.6	6816
0.6-0.7	9409
0.7-0.8	2442
0.8-0.85	98
0.85-0.9	18
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.984	High Similarity	NPC59239
0.9603	High Similarity	NPC78575
0.9297	High Similarity	NPC312341
0.8984	High Similarity	NPC471077
0.8976	High Similarity	NPC124030
0.8947	High Similarity	NPC68292
0.8913	High Similarity	NPC84786
0.8864	High Similarity	NPC227719
0.881	High Similarity	NPC474115
0.8788	High Similarity	NPC321086
0.8786	High Similarity	NPC127046
0.874	High Similarity	NPC471794
0.8714	High Similarity	NPC474991
0.8692	High Similarity	NPC186889
0.8633	High Similarity	NPC473845
0.8626	High Similarity	NPC201069
0.8626	High Similarity	NPC223912
0.8615	High Similarity	NPC470724
0.8583	High Similarity	NPC470414
0.8571	High Similarity	NPC469644
0.8551	High Similarity	NPC265075
0.8531	High Similarity	NPC183380
0.8504	High Similarity	NPC260832
0.8504	High Similarity	NPC135467
0.85	High Similarity	NPC473108
0.8492	Intermediate Similarity	NPC471671
0.8483	Intermediate Similarity	NPC475227
0.8483	Intermediate Similarity	NPC200645
0.8483	Intermediate Similarity	NPC106669
0.8473	Intermediate Similarity	NPC321822
0.8473	Intermediate Similarity	NPC100414
0.8473	Intermediate Similarity	NPC325294
0.8473	Intermediate Similarity	NPC43000
0.8455	Intermediate Similarity	NPC471179
0.8451	Intermediate Similarity	NPC474397
0.8451	Intermediate Similarity	NPC246229
0.8451	Intermediate Similarity	NPC191899
0.844	Intermediate Similarity	NPC90645
0.844	Intermediate Similarity	NPC472457
0.8413	Intermediate Similarity	NPC304510
0.8413	Intermediate Similarity	NPC16030
0.8413	Intermediate Similarity	NPC172219
0.8409	Intermediate Similarity	NPC476536
0.8409	Intermediate Similarity	NPC108164
0.8406	Intermediate Similarity	NPC32630
0.8397	Intermediate Similarity	NPC476653
0.8397	Intermediate Similarity	NPC470726
0.8394	Intermediate Similarity	NPC470733
0.8392	Intermediate Similarity	NPC473876
0.8387	Intermediate Similarity	NPC317869
0.8382	Intermediate Similarity	NPC471942
0.838	Intermediate Similarity	NPC233980
0.837	Intermediate Similarity	NPC165612
0.837	Intermediate Similarity	NPC228843
0.8369	Intermediate Similarity	NPC164183
0.8358	Intermediate Similarity	NPC196193
0.8358	Intermediate Similarity	NPC470727
0.8357	Intermediate Similarity	NPC186033
0.8346	Intermediate Similarity	NPC469609
0.8346	Intermediate Similarity	NPC154030
0.8345	Intermediate Similarity	NPC2745
0.8333	Intermediate Similarity	NPC308311
0.8333	Intermediate Similarity	NPC92
0.8333	Intermediate Similarity	NPC469663
0.8333	Intermediate Similarity	NPC477137
0.8333	Intermediate Similarity	NPC38893
0.8309	Intermediate Similarity	NPC474453
0.8288	Intermediate Similarity	NPC325860
0.8288	Intermediate Similarity	NPC157783
0.8286	Intermediate Similarity	NPC35216
0.8284	Intermediate Similarity	NPC470747
0.8276	Intermediate Similarity	NPC158784
0.8276	Intermediate Similarity	NPC195561
0.8273	Intermediate Similarity	NPC474640
0.8273	Intermediate Similarity	NPC475757
0.8268	Intermediate Similarity	NPC477136
0.8261	Intermediate Similarity	NPC234952
0.8254	Intermediate Similarity	NPC192948
0.8254	Intermediate Similarity	NPC35797
0.8248	Intermediate Similarity	NPC311256
0.8248	Intermediate Similarity	NPC193026
0.8248	Intermediate Similarity	NPC187616
0.8248	Intermediate Similarity	NPC49603
0.8244	Intermediate Similarity	NPC473451
0.8239	Intermediate Similarity	NPC133251
0.8235	Intermediate Similarity	NPC303144
0.8222	Intermediate Similarity	NPC143483
0.8219	Intermediate Similarity	NPC302915
0.8217	Intermediate Similarity	NPC3239
0.8217	Intermediate Similarity	NPC282255
0.8209	Intermediate Similarity	NPC472968
0.8189	Intermediate Similarity	NPC219112
0.8189	Intermediate Similarity	NPC308828
0.8188	Intermediate Similarity	NPC473413
0.8182	Intermediate Similarity	NPC146355
0.8182	Intermediate Similarity	NPC126707
0.8182	Intermediate Similarity	NPC257682
0.8182	Intermediate Similarity	NPC131747
0.8169	Intermediate Similarity	NPC472451
0.8168	Intermediate Similarity	NPC321402
0.8168	Intermediate Similarity	NPC152946
0.8163	Intermediate Similarity	NPC160196
0.8156	Intermediate Similarity	NPC71046
0.8143	Intermediate Similarity	NPC230124
0.8143	Intermediate Similarity	NPC6300
0.8143	Intermediate Similarity	NPC114171
0.8143	Intermediate Similarity	NPC184613
0.8143	Intermediate Similarity	NPC260741
0.8143	Intermediate Similarity	NPC70682
0.814	Intermediate Similarity	NPC176893
0.8138	Intermediate Similarity	NPC474795
0.8138	Intermediate Similarity	NPC303013
0.8138	Intermediate Similarity	NPC474940
0.8138	Intermediate Similarity	NPC159697
0.8138	Intermediate Similarity	NPC130959
0.8138	Intermediate Similarity	NPC179809
0.8138	Intermediate Similarity	NPC212142
0.8134	Intermediate Similarity	NPC21563
0.8129	Intermediate Similarity	NPC29799
0.8129	Intermediate Similarity	NPC477939
0.8129	Intermediate Similarity	NPC472800
0.8129	Intermediate Similarity	NPC156502
0.8129	Intermediate Similarity	NPC54743
0.8129	Intermediate Similarity	NPC10737
0.8129	Intermediate Similarity	NPC209985
0.8129	Intermediate Similarity	NPC177160
0.8129	Intermediate Similarity	NPC263367
0.8129	Intermediate Similarity	NPC470802
0.812	Intermediate Similarity	NPC76119
0.812	Intermediate Similarity	NPC293801
0.812	Intermediate Similarity	NPC4286
0.8116	Intermediate Similarity	NPC209199
0.8116	Intermediate Similarity	NPC473107
0.8116	Intermediate Similarity	NPC478085
0.8112	Intermediate Similarity	NPC50250
0.8112	Intermediate Similarity	NPC469795
0.811	Intermediate Similarity	NPC147179
0.8102	Intermediate Similarity	NPC321502
0.8099	Intermediate Similarity	NPC475891
0.8099	Intermediate Similarity	NPC2613
0.8099	Intermediate Similarity	NPC204347
0.8099	Intermediate Similarity	NPC59841
0.8085	Intermediate Similarity	NPC259519
0.8085	Intermediate Similarity	NPC308768
0.8085	Intermediate Similarity	NPC12668
0.8082	Intermediate Similarity	NPC181452
0.8082	Intermediate Similarity	NPC220006
0.808	Intermediate Similarity	NPC260323
0.808	Intermediate Similarity	NPC176279
0.8077	Intermediate Similarity	NPC475245
0.8074	Intermediate Similarity	NPC11258
0.8074	Intermediate Similarity	NPC21867
0.8074	Intermediate Similarity	NPC311293
0.8074	Intermediate Similarity	NPC252307
0.8074	Intermediate Similarity	NPC184733
0.8074	Intermediate Similarity	NPC128208
0.8074	Intermediate Similarity	NPC474178
0.8074	Intermediate Similarity	NPC307050
0.8074	Intermediate Similarity	NPC245826
0.8074	Intermediate Similarity	NPC148366
0.8074	Intermediate Similarity	NPC129570
0.8074	Intermediate Similarity	NPC277458
0.8074	Intermediate Similarity	NPC45774
0.8074	Intermediate Similarity	NPC282703
0.8071	Intermediate Similarity	NPC22902
0.8071	Intermediate Similarity	NPC211549
0.8071	Intermediate Similarity	NPC242715
0.8071	Intermediate Similarity	NPC56329
0.8069	Intermediate Similarity	NPC101376
0.8069	Intermediate Similarity	NPC58752
0.8058	Intermediate Similarity	NPC313081
0.8056	Intermediate Similarity	NPC272619
0.8056	Intermediate Similarity	NPC469557
0.8056	Intermediate Similarity	NPC286245
0.8054	Intermediate Similarity	NPC188578
0.8054	Intermediate Similarity	NPC80918
0.8047	Intermediate Similarity	NPC471668
0.8045	Intermediate Similarity	NPC224342
0.8043	Intermediate Similarity	NPC49742
0.8043	Intermediate Similarity	NPC11060
0.8043	Intermediate Similarity	NPC170185
0.8042	Intermediate Similarity	NPC47633
0.8042	Intermediate Similarity	NPC85264
0.8042	Intermediate Similarity	NPC102044
0.8031	Intermediate Similarity	NPC268160
0.8029	Intermediate Similarity	NPC15543
0.8029	Intermediate Similarity	NPC291001
0.8027	Intermediate Similarity	NPC225815
0.8027	Intermediate Similarity	NPC260781
0.8027	Intermediate Similarity	NPC469706
0.8027	Intermediate Similarity	NPC469707
0.8027	Intermediate Similarity	NPC185955
0.8027	Intermediate Similarity	NPC9933
0.8027	Intermediate Similarity	NPC214326
0.8027	Intermediate Similarity	NPC218041
0.8027	Intermediate Similarity	NPC145979
0.8027	Intermediate Similarity	NPC182368
0.8016	Intermediate Similarity	NPC250323
0.8014	Intermediate Similarity	NPC220344
0.8014	Intermediate Similarity	NPC243996

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 NPC99795 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	854
0.2-0.3	1642
0.3-0.4	2882
0.4-0.5	1867
0.5-0.6	1019
0.6-0.7	472
0.7-0.8	60
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8252	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD3620	Phase 2
0.8028	Intermediate Similarity	NPD6674	Discontinued
0.8014	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD3092	Approved
0.7778	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD2861	Phase 2
0.7721	Intermediate Similarity	NPD3094	Phase 2
0.7714	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1613	Approved
0.7698	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD3091	Approved
0.7647	Intermediate Similarity	NPD6696	Suspended
0.7638	Intermediate Similarity	NPD3022	Approved
0.7638	Intermediate Similarity	NPD3021	Approved
0.7626	Intermediate Similarity	NPD4625	Phase 3
0.7626	Intermediate Similarity	NPD3027	Phase 3
0.7609	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7635	Approved
0.7571	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD5735	Approved
0.7517	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7266	Discontinued
0.7483	Intermediate Similarity	NPD8166	Discontinued
0.7465	Intermediate Similarity	NPD4060	Phase 1
0.7445	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4749	Approved
0.7429	Intermediate Similarity	NPD4908	Phase 1
0.7407	Intermediate Similarity	NPD5125	Phase 3
0.7407	Intermediate Similarity	NPD5126	Approved
0.7375	Intermediate Similarity	NPD2489	Approved
0.7375	Intermediate Similarity	NPD27	Approved
0.7368	Intermediate Similarity	NPD7340	Approved
0.7361	Intermediate Similarity	NPD4097	Suspended
0.7357	Intermediate Similarity	NPD5736	Approved
0.7344	Intermediate Similarity	NPD2342	Discontinued
0.7319	Intermediate Similarity	NPD5327	Phase 3
0.7312	Intermediate Similarity	NPD2969	Approved
0.7312	Intermediate Similarity	NPD2970	Approved
0.7299	Intermediate Similarity	NPD1610	Phase 2
0.7284	Intermediate Similarity	NPD7228	Approved
0.7279	Intermediate Similarity	NPD4626	Approved
0.7279	Intermediate Similarity	NPD3095	Discontinued
0.7278	Intermediate Similarity	NPD6234	Discontinued
0.7273	Intermediate Similarity	NPD1398	Phase 1
0.7266	Intermediate Similarity	NPD8651	Approved
0.7252	Intermediate Similarity	NPD228	Approved
0.725	Intermediate Similarity	NPD3051	Approved
0.7244	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1809	Phase 2
0.7231	Intermediate Similarity	NPD4750	Phase 3
0.7222	Intermediate Similarity	NPD4140	Approved
0.7211	Intermediate Similarity	NPD6099	Approved
0.7211	Intermediate Similarity	NPD6100	Approved
0.7206	Intermediate Similarity	NPD5691	Approved
0.7174	Intermediate Similarity	NPD3705	Approved
0.7172	Intermediate Similarity	NPD3657	Discovery
0.7163	Intermediate Similarity	NPD4624	Approved
0.7153	Intermediate Similarity	NPD4059	Approved
0.7153	Intermediate Similarity	NPD3019	Approved
0.7153	Intermediate Similarity	NPD6663	Approved
0.7153	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5283	Phase 1
0.7132	Intermediate Similarity	NPD7741	Discontinued
0.7126	Intermediate Similarity	NPD7312	Approved
0.7126	Intermediate Similarity	NPD4577	Approved
0.7126	Intermediate Similarity	NPD7313	Approved
0.7126	Intermediate Similarity	NPD4578	Approved
0.7126	Intermediate Similarity	NPD7310	Approved
0.7126	Intermediate Similarity	NPD7311	Approved
0.7123	Intermediate Similarity	NPD6353	Approved
0.7083	Intermediate Similarity	NPD7309	Approved
0.707	Intermediate Similarity	NPD37	Approved
0.7063	Intermediate Similarity	NPD3020	Approved
0.7047	Intermediate Similarity	NPD5763	Approved
0.7047	Intermediate Similarity	NPD5762	Approved
0.7044	Intermediate Similarity	NPD4967	Phase 2
0.7044	Intermediate Similarity	NPD4965	Approved
0.7044	Intermediate Similarity	NPD4966	Approved
0.704	Intermediate Similarity	NPD288	Approved
0.7037	Intermediate Similarity	NPD6671	Approved
0.703	Intermediate Similarity	NPD5844	Phase 1
0.7015	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4663	Approved
0.6993	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7041	Phase 2
0.6992	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6959	Discontinued
0.6962	Remote Similarity	NPD1934	Approved
0.696	Remote Similarity	NPD844	Approved
0.6959	Remote Similarity	NPD7906	Approved
0.6948	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3645	Discontinued
0.6937	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD845	Approved
0.6913	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7157	Approved
0.6908	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7003	Approved
0.6901	Remote Similarity	NPD1283	Approved
0.6884	Remote Similarity	NPD1548	Phase 1
0.6883	Remote Similarity	NPD2421	Approved
0.6883	Remote Similarity	NPD2420	Approved
0.688	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD8127	Discontinued
0.6871	Remote Similarity	NPD2238	Phase 2
0.6863	Remote Similarity	NPD2677	Approved
0.6848	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6166	Phase 2
0.6846	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4536	Approved
0.6846	Remote Similarity	NPD4538	Approved
0.6835	Remote Similarity	NPD1651	Approved
0.6835	Remote Similarity	NPD1357	Approved
0.6831	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6232	Discontinued
0.6828	Remote Similarity	NPD2606	Approved
0.6828	Remote Similarity	NPD2605	Approved
0.6825	Remote Similarity	NPD2859	Approved
0.6825	Remote Similarity	NPD2860	Approved
0.6824	Remote Similarity	NPD5124	Phase 1
0.6824	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5929	Approved
0.6809	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7473	Discontinued
0.6805	Remote Similarity	NPD7240	Approved
0.68	Remote Similarity	NPD1753	Discontinued
0.6797	Remote Similarity	NPD4628	Phase 3
0.6797	Remote Similarity	NPD4110	Phase 3
0.6797	Remote Similarity	NPD6331	Phase 2
0.6797	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7833	Phase 2
0.679	Remote Similarity	NPD7831	Phase 2
0.679	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4198	Discontinued
0.6786	Remote Similarity	NPD1751	Approved
0.6786	Remote Similarity	NPD2286	Discontinued
0.6786	Remote Similarity	NPD9384	Approved
0.6786	Remote Similarity	NPD1778	Approved
0.6786	Remote Similarity	NPD9381	Approved
0.6782	Remote Similarity	NPD2490	Approved
0.6782	Remote Similarity	NPD2488	Approved
0.6781	Remote Similarity	NPD5156	Approved
0.6781	Remote Similarity	NPD5155	Approved
0.6776	Remote Similarity	NPD7037	Approved
0.677	Remote Similarity	NPD2563	Approved
0.677	Remote Similarity	NPD2560	Approved
0.6769	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD2684	Approved
0.6761	Remote Similarity	NPD2232	Approved
0.6761	Remote Similarity	NPD2230	Approved
0.6761	Remote Similarity	NPD2233	Approved
0.6759	Remote Similarity	NPD3636	Approved
0.6759	Remote Similarity	NPD3637	Approved
0.6759	Remote Similarity	NPD3635	Approved
0.6757	Remote Similarity	NPD1558	Phase 1
0.6757	Remote Similarity	NPD2979	Phase 3
0.6753	Remote Similarity	NPD6190	Approved
0.6747	Remote Similarity	NPD4481	Phase 3
0.6746	Remote Similarity	NPD2934	Approved
0.6746	Remote Similarity	NPD2933	Approved
0.6744	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7294	Phase 1
0.6735	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7985	Registered
0.6732	Remote Similarity	NPD5177	Phase 3
0.6731	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2532	Approved
0.6731	Remote Similarity	NPD2534	Approved
0.6731	Remote Similarity	NPD2533	Approved
0.673	Remote Similarity	NPD4380	Phase 2
0.6727	Remote Similarity	NPD6071	Discontinued
0.6714	Remote Similarity	NPD4093	Discontinued
0.6713	Remote Similarity	NPD9622	Approved
0.6712	Remote Similarity	NPD3595	Approved
0.6712	Remote Similarity	NPD3594	Approved
0.6711	Remote Similarity	NPD4726	Approved
0.6711	Remote Similarity	NPD4725	Approved
0.6711	Remote Similarity	NPD230	Phase 1
0.6711	Remote Similarity	NPD4721	Approved
0.6709	Remote Similarity	NPD1653	Approved
0.6708	Remote Similarity	NPD1465	Phase 2
0.6707	Remote Similarity	NPD5494	Approved
0.6707	Remote Similarity	NPD4666	Phase 3
0.6692	Remote Similarity	NPD846	Approved
0.6692	Remote Similarity	NPD940	Approved
0.6691	Remote Similarity	NPD7644	Approved
0.669	Remote Similarity	NPD6584	Phase 3
0.669	Remote Similarity	NPD1091	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