NPASS Compound

Structure

NPC470727 OpenBabel07101719152D 21 22 0 0 1 0 0 0 0 0999 V2000 0.4288 -1.6003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5242 -0.1812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4783 2.7414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1419 1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6567 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6567 1.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6764 -0.6764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4851 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4851 1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8284 1.4348 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8284 0.4783 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 1.9130 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6567 1.9130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6567 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4783 2.7414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8837 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3135 1.9130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 5 21 1 0 0 0 0 6 9 1 0 0 0 0 6 11 2 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 4 1 1 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.16
Volume:	304.221
LogP:	1.671
LogD:	1.451
LogS:	-2.983
# Rotatable Bonds:	2
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.648
Synthetic Accessibility Score:	4.197
Fsp3:	0.625
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:	-4.737
MDCK Permeability:	7.455390004906803e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.322
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.852
30% Bioavailability (F30%):	0.39

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	66.41826629638672%
Volume Distribution (VD):	1.473
Pgp-substrate:	25.247447967529297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.264
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.374
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.376
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.323

ADMET: Excretion

Clearance (CL):	5.111
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.169
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.021
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC470727

Natural Product ID:	NPC470727
*Common Name:**	(1R)-7-Methoxy-1,6-Dimethyl-4-Propan-2-Yl-2,3-Dihydronaphthalene-1,2,3,4-Tetrol
IUPAC Name:	(1R)-7-methoxy-1,6-dimethyl-4-propan-2-yl-2,3-dihydronaphthalene-1,2,3,4-tetrol
Synonyms:
Standard InCHIKey:	ZVZHQJHYUIHXPZ-MYLOQMAZSA-N
Standard InCHI:	InChI=1S/C16H24O5/c1-8(2)16(20)11-6-9(3)12(21-5)7-10(11)15(4,19)13(17)14(16)18/h6-8,13-14,17-20H,1-5H3/t13?,14?,15-,16?/m1/s1
SMILES:	COc1cc2c(cc1C)C(O)(C(C)C)C(C([C@]2(C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2206803
PubChem CID:	71459705
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32770	sterculia tavia	Species	Malvaceae	Eukaryota	n.a.	Madagascar Rain Forest	n.a.	PMID[23149304]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	35500.0	nM	PMID[468031]

☑ 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 NPC470727 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	374
0.1-0.2	1411
0.2-0.3	3708
0.3-0.4	9525
0.4-0.5	9420
0.5-0.6	4298
0.6-0.7	9648
0.7-0.8	3691
0.8-0.85	579
0.85-0.9	40
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9675	High Similarity	NPC470724
0.9435	High Similarity	NPC470726
0.8947	High Similarity	NPC472800
0.8947	High Similarity	NPC327735
0.8939	High Similarity	NPC16485
0.8806	High Similarity	NPC68292
0.8806	High Similarity	NPC126101
0.8797	High Similarity	NPC311256
0.8705	High Similarity	NPC221318
0.8692	High Similarity	NPC186889
0.8692	High Similarity	NPC471077
0.8686	High Similarity	NPC265075
0.8682	High Similarity	NPC4286
0.8682	High Similarity	NPC105031
0.8682	High Similarity	NPC76119
0.8682	High Similarity	NPC293801
0.8676	High Similarity	NPC6300
0.8676	High Similarity	NPC114171
0.8676	High Similarity	NPC184613
0.8676	High Similarity	NPC230124
0.8647	High Similarity	NPC18842
0.8636	High Similarity	NPC196193
0.8636	High Similarity	NPC143483
0.8626	High Similarity	NPC472968
0.8615	High Similarity	NPC82299
0.8603	High Similarity	NPC3072
0.8603	High Similarity	NPC46277
0.8603	High Similarity	NPC156948
0.8603	High Similarity	NPC301765
0.8603	High Similarity	NPC86605
0.8594	High Similarity	NPC152946
0.8593	High Similarity	NPC256262
0.8583	High Similarity	NPC129176
0.8582	High Similarity	NPC26394
0.8582	High Similarity	NPC474397
0.8582	High Similarity	NPC227719
0.8571	High Similarity	NPC15543
0.8571	High Similarity	NPC312341
0.8571	High Similarity	NPC472457
0.8561	High Similarity	NPC472797
0.8561	High Similarity	NPC258083
0.855	High Similarity	NPC118533
0.855	High Similarity	NPC5428
0.855	High Similarity	NPC473221
0.855	High Similarity	NPC165045
0.855	High Similarity	NPC469386
0.854	High Similarity	NPC32630
0.8531	High Similarity	NPC158784
0.8529	High Similarity	NPC263367
0.8529	High Similarity	NPC54743
0.8529	High Similarity	NPC10737
0.8529	High Similarity	NPC133025
0.8529	High Similarity	NPC477939
0.8529	High Similarity	NPC177160
0.8529	High Similarity	NPC209985
0.8529	High Similarity	NPC29799
0.8529	High Similarity	NPC156502
0.8527	High Similarity	NPC474160
0.8519	High Similarity	NPC209199
0.8511	High Similarity	NPC233980
0.8507	High Similarity	NPC228843
0.8507	High Similarity	NPC230219
0.8507	High Similarity	NPC59239
0.8507	High Similarity	NPC472798
0.85	High Similarity	NPC473845
0.8496	Intermediate Similarity	NPC11089
0.8489	Intermediate Similarity	NPC175838
0.8489	Intermediate Similarity	NPC186033
0.8489	Intermediate Similarity	NPC470917
0.8485	Intermediate Similarity	NPC470084
0.8478	Intermediate Similarity	NPC12668
0.8478	Intermediate Similarity	NPC308768
0.8472	Intermediate Similarity	NPC2745
0.8472	Intermediate Similarity	NPC302915
0.8467	Intermediate Similarity	NPC477938
0.8467	Intermediate Similarity	NPC56329
0.8467	Intermediate Similarity	NPC266006
0.8467	Intermediate Similarity	NPC242715
0.8467	Intermediate Similarity	NPC22902
0.8456	Intermediate Similarity	NPC180602
0.8456	Intermediate Similarity	NPC240279
0.8456	Intermediate Similarity	NPC55239
0.8456	Intermediate Similarity	NPC214853
0.8456	Intermediate Similarity	NPC313081
0.845	Intermediate Similarity	NPC77789
0.845	Intermediate Similarity	NPC57199
0.845	Intermediate Similarity	NPC18128
0.844	Intermediate Similarity	NPC90645
0.8433	Intermediate Similarity	NPC277804
0.8433	Intermediate Similarity	NPC78575
0.8433	Intermediate Similarity	NPC160623
0.8433	Intermediate Similarity	NPC474017
0.8429	Intermediate Similarity	NPC477616
0.8421	Intermediate Similarity	NPC472795
0.8421	Intermediate Similarity	NPC472796
0.8417	Intermediate Similarity	NPC71046
0.8417	Intermediate Similarity	NPC87725
0.8417	Intermediate Similarity	NPC263261
0.8414	Intermediate Similarity	NPC160196
0.8414	Intermediate Similarity	NPC157783
0.8414	Intermediate Similarity	NPC325860
0.8409	Intermediate Similarity	NPC242032
0.8409	Intermediate Similarity	NPC21563
0.8406	Intermediate Similarity	NPC132804
0.8406	Intermediate Similarity	NPC220344
0.8406	Intermediate Similarity	NPC243759
0.8406	Intermediate Similarity	NPC471183
0.8406	Intermediate Similarity	NPC79622
0.8406	Intermediate Similarity	NPC212942
0.8406	Intermediate Similarity	NPC243996
0.8406	Intermediate Similarity	NPC29868
0.8406	Intermediate Similarity	NPC275061
0.8406	Intermediate Similarity	NPC105847
0.8406	Intermediate Similarity	NPC218131
0.8403	Intermediate Similarity	NPC195561
0.8397	Intermediate Similarity	NPC124030
0.8397	Intermediate Similarity	NPC81641
0.8397	Intermediate Similarity	NPC148627
0.8394	Intermediate Similarity	NPC470802
0.8394	Intermediate Similarity	NPC143139
0.8394	Intermediate Similarity	NPC234952
0.8394	Intermediate Similarity	NPC205442
0.8394	Intermediate Similarity	NPC30632
0.8394	Intermediate Similarity	NPC202846
0.8392	Intermediate Similarity	NPC212142
0.8382	Intermediate Similarity	NPC206737
0.8382	Intermediate Similarity	NPC56764
0.8382	Intermediate Similarity	NPC125649
0.8382	Intermediate Similarity	NPC276026
0.8382	Intermediate Similarity	NPC188378
0.8382	Intermediate Similarity	NPC555
0.8382	Intermediate Similarity	NPC469659
0.8382	Intermediate Similarity	NPC471942
0.8382	Intermediate Similarity	NPC7515
0.8382	Intermediate Similarity	NPC473107
0.8382	Intermediate Similarity	NPC289258
0.8382	Intermediate Similarity	NPC187616
0.8382	Intermediate Similarity	NPC49603
0.8382	Intermediate Similarity	NPC193026
0.838	Intermediate Similarity	NPC471608
0.838	Intermediate Similarity	NPC274454
0.838	Intermediate Similarity	NPC112251
0.838	Intermediate Similarity	NPC215678
0.8372	Intermediate Similarity	NPC476633
0.837	Intermediate Similarity	NPC14224
0.837	Intermediate Similarity	NPC102256
0.837	Intermediate Similarity	NPC161958
0.837	Intermediate Similarity	NPC6451
0.8369	Intermediate Similarity	NPC50250
0.8369	Intermediate Similarity	NPC164183
0.8369	Intermediate Similarity	NPC473108
0.8369	Intermediate Similarity	NPC469795
0.8358	Intermediate Similarity	NPC42300
0.8358	Intermediate Similarity	NPC241522
0.8358	Intermediate Similarity	NPC242807
0.8358	Intermediate Similarity	NPC92164
0.8358	Intermediate Similarity	NPC192687
0.8358	Intermediate Similarity	NPC145305
0.8358	Intermediate Similarity	NPC174495
0.8358	Intermediate Similarity	NPC99795
0.8358	Intermediate Similarity	NPC224157
0.8358	Intermediate Similarity	NPC187998
0.8358	Intermediate Similarity	NPC64201
0.8358	Intermediate Similarity	NPC77040
0.8358	Intermediate Similarity	NPC153739
0.8358	Intermediate Similarity	NPC126836
0.8358	Intermediate Similarity	NPC257582
0.8346	Intermediate Similarity	NPC38604
0.8346	Intermediate Similarity	NPC215300
0.8346	Intermediate Similarity	NPC211179
0.8346	Intermediate Similarity	NPC307050
0.8346	Intermediate Similarity	NPC28765
0.8346	Intermediate Similarity	NPC38017
0.8346	Intermediate Similarity	NPC277458
0.8346	Intermediate Similarity	NPC223912
0.8345	Intermediate Similarity	NPC34431
0.8345	Intermediate Similarity	NPC73505
0.8345	Intermediate Similarity	NPC259519
0.8345	Intermediate Similarity	NPC165026
0.8345	Intermediate Similarity	NPC295719
0.8333	Intermediate Similarity	NPC6100
0.8333	Intermediate Similarity	NPC206882
0.8333	Intermediate Similarity	NPC156888
0.8333	Intermediate Similarity	NPC470721
0.8333	Intermediate Similarity	NPC266453
0.8333	Intermediate Similarity	NPC170485
0.8333	Intermediate Similarity	NPC151656
0.8333	Intermediate Similarity	NPC200935
0.8333	Intermediate Similarity	NPC230919
0.8333	Intermediate Similarity	NPC470722
0.8322	Intermediate Similarity	NPC174251
0.8322	Intermediate Similarity	NPC116019
0.8322	Intermediate Similarity	NPC101376
0.8322	Intermediate Similarity	NPC153182
0.8321	Intermediate Similarity	NPC69029
0.8321	Intermediate Similarity	NPC294884
0.8321	Intermediate Similarity	NPC158142
0.8321	Intermediate Similarity	NPC473413
0.8321	Intermediate Similarity	NPC108198
0.8321	Intermediate Similarity	NPC10314

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 NPC470727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	869
0.2-0.3	1912
0.3-0.4	2732
0.4-0.5	1626
0.5-0.6	956
0.6-0.7	620
0.7-0.8	105
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8417	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD3027	Phase 3
0.8156	Intermediate Similarity	NPD6674	Discontinued
0.8148	Intermediate Similarity	NPD4625	Phase 3
0.8106	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD6696	Suspended
0.8	Intermediate Similarity	NPD2861	Phase 2
0.7971	Intermediate Similarity	NPD4060	Phase 1
0.7971	Intermediate Similarity	NPD1613	Approved
0.7971	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD2238	Phase 2
0.7971	Intermediate Similarity	NPD3620	Phase 2
0.797	Intermediate Similarity	NPD4749	Approved
0.7956	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4626	Approved
0.781	Intermediate Similarity	NPD4908	Phase 1
0.7786	Intermediate Similarity	NPD5735	Approved
0.7769	Intermediate Similarity	NPD7340	Approved
0.7762	Intermediate Similarity	NPD5763	Approved
0.7762	Intermediate Similarity	NPD5762	Approved
0.7748	Intermediate Similarity	NPD37	Approved
0.7737	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4097	Suspended
0.7727	Intermediate Similarity	NPD5691	Approved
0.7721	Intermediate Similarity	NPD3094	Phase 2
0.7687	Intermediate Similarity	NPD1610	Phase 2
0.7681	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5283	Phase 1
0.7674	Intermediate Similarity	NPD1398	Phase 1
0.7647	Intermediate Similarity	NPD8651	Approved
0.7597	Intermediate Similarity	NPD4967	Phase 2
0.7597	Intermediate Similarity	NPD4966	Approved
0.7597	Intermediate Similarity	NPD4965	Approved
0.7597	Intermediate Similarity	NPD7635	Approved
0.7557	Intermediate Similarity	NPD6671	Approved
0.7556	Intermediate Similarity	NPD3705	Approved
0.7556	Intermediate Similarity	NPD3092	Approved
0.7551	Intermediate Similarity	NPD2677	Approved
0.7536	Intermediate Similarity	NPD4624	Approved
0.7518	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD2233	Approved
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD2230	Approved
0.75	Intermediate Similarity	NPD2232	Approved
0.7465	Intermediate Similarity	NPD4140	Approved
0.7463	Intermediate Similarity	NPD1651	Approved
0.7453	Intermediate Similarity	NPD5844	Phase 1
0.7448	Intermediate Similarity	NPD6099	Approved
0.7448	Intermediate Similarity	NPD6100	Approved
0.7447	Intermediate Similarity	NPD7985	Registered
0.7445	Intermediate Similarity	NPD5327	Phase 3
0.7431	Intermediate Similarity	NPD4536	Approved
0.7431	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4538	Approved
0.7426	Intermediate Similarity	NPD1091	Approved
0.7426	Intermediate Similarity	NPD1611	Approved
0.7424	Intermediate Similarity	NPD7157	Approved
0.7422	Intermediate Similarity	NPD2684	Approved
0.7413	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5124	Phase 1
0.7407	Intermediate Similarity	NPD5126	Approved
0.7407	Intermediate Similarity	NPD5125	Phase 3
0.7388	Intermediate Similarity	NPD3091	Approved
0.7388	Intermediate Similarity	NPD1548	Phase 1
0.7385	Intermediate Similarity	NPD228	Approved
0.7364	Intermediate Similarity	NPD3022	Approved
0.7364	Intermediate Similarity	NPD3021	Approved
0.7361	Intermediate Similarity	NPD6353	Approved
0.7357	Intermediate Similarity	NPD3018	Phase 2
0.7355	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD290	Approved
0.7343	Intermediate Similarity	NPD2979	Phase 3
0.7333	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7041	Phase 2
0.7329	Intermediate Similarity	NPD2438	Suspended
0.7328	Intermediate Similarity	NPD7843	Approved
0.7324	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1281	Approved
0.7292	Intermediate Similarity	NPD3657	Discovery
0.7285	Intermediate Similarity	NPD2534	Approved
0.7285	Intermediate Similarity	NPD2532	Approved
0.7285	Intermediate Similarity	NPD2533	Approved
0.7284	Intermediate Similarity	NPD7228	Approved
0.7279	Intermediate Similarity	NPD3095	Discontinued
0.7279	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5058	Phase 3
0.726	Intermediate Similarity	NPD5588	Approved
0.726	Intermediate Similarity	NPD5960	Phase 3
0.7259	Intermediate Similarity	NPD7741	Discontinued
0.725	Intermediate Similarity	NPD6232	Discontinued
0.7248	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7248	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3892	Phase 2
0.7244	Intermediate Similarity	NPD5929	Approved
0.7237	Intermediate Similarity	NPD6090	Discontinued
0.7237	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4666	Phase 3
0.723	Intermediate Similarity	NPD2424	Discontinued
0.7222	Intermediate Similarity	NPD7473	Discontinued
0.7211	Intermediate Similarity	NPD2935	Discontinued
0.7194	Intermediate Similarity	NPD2982	Phase 2
0.7194	Intermediate Similarity	NPD1669	Approved
0.7194	Intermediate Similarity	NPD2983	Phase 2
0.7188	Intermediate Similarity	NPD6959	Discontinued
0.7185	Intermediate Similarity	NPD7644	Approved
0.7172	Intermediate Similarity	NPD6355	Discontinued
0.7171	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5709	Phase 3
0.7162	Intermediate Similarity	NPD6005	Phase 3
0.7162	Intermediate Similarity	NPD6002	Phase 3
0.7162	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6004	Phase 3
0.7162	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4380	Phase 2
0.7153	Intermediate Similarity	NPD2667	Approved
0.7153	Intermediate Similarity	NPD2668	Approved
0.7143	Intermediate Similarity	NPD4108	Discontinued
0.7143	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2675	Approved
0.7124	Intermediate Similarity	NPD2676	Approved
0.7123	Intermediate Similarity	NPD2157	Approved
0.7122	Intermediate Similarity	NPD2981	Phase 2
0.7122	Intermediate Similarity	NPD2231	Phase 2
0.7122	Intermediate Similarity	NPD2235	Phase 2
0.7114	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4663	Approved
0.7101	Intermediate Similarity	NPD3496	Discontinued
0.7099	Intermediate Similarity	NPD2969	Approved
0.7099	Intermediate Similarity	NPD2970	Approved
0.7097	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4005	Discontinued
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7199	Phase 2
0.708	Intermediate Similarity	NPD1357	Approved
0.7077	Intermediate Similarity	NPD2342	Discontinued
0.7071	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1934	Approved
0.7067	Intermediate Similarity	NPD5177	Phase 3
0.7063	Intermediate Similarity	NPD3020	Approved
0.7042	Intermediate Similarity	NPD3691	Phase 2
0.7042	Intermediate Similarity	NPD3690	Phase 2
0.704	Intermediate Similarity	NPD288	Approved
0.7039	Intermediate Similarity	NPD6666	Approved
0.7039	Intermediate Similarity	NPD6667	Approved
0.7037	Intermediate Similarity	NPD3051	Approved
0.7037	Intermediate Similarity	NPD3787	Discontinued
0.7037	Intermediate Similarity	NPD709	Approved
0.7032	Intermediate Similarity	NPD1653	Approved
0.7029	Intermediate Similarity	NPD1778	Approved
0.7027	Intermediate Similarity	NPD7033	Discontinued
0.7025	Intermediate Similarity	NPD7819	Suspended
0.702	Intermediate Similarity	NPD7003	Approved
0.7014	Intermediate Similarity	NPD7095	Approved
0.7007	Intermediate Similarity	NPD6653	Approved
0.7006	Intermediate Similarity	NPD7240	Approved
0.7006	Intermediate Similarity	NPD6072	Discontinued
0.7	Intermediate Similarity	NPD968	Approved
0.6981	Remote Similarity	NPD2563	Approved
0.6981	Remote Similarity	NPD2560	Approved
0.698	Remote Similarity	NPD2531	Phase 2
0.6966	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5111	Phase 2
0.6966	Remote Similarity	NPD5110	Phase 2
0.6966	Remote Similarity	NPD6798	Discontinued
0.6966	Remote Similarity	NPD5109	Approved
0.6963	Remote Similarity	NPD497	Approved
0.696	Remote Similarity	NPD844	Approved
0.6959	Remote Similarity	NPD7097	Phase 1
0.6959	Remote Similarity	NPD7906	Approved
0.6954	Remote Similarity	NPD1652	Phase 2
0.6954	Remote Similarity	NPD4236	Phase 3
0.6954	Remote Similarity	NPD3060	Approved
0.6954	Remote Similarity	NPD4237	Approved
0.6953	Remote Similarity	NPD940	Approved
0.6953	Remote Similarity	NPD846	Approved
0.6951	Remote Similarity	NPD2489	Approved
0.6951	Remote Similarity	NPD27	Approved
0.6948	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD600	Approved
0.6944	Remote Similarity	NPD596	Approved
0.6941	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1138	Approved
0.6937	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7266	Discontinued
0.6933	Remote Similarity	NPD7229	Phase 3
0.6929	Remote Similarity	NPD422	Phase 1
0.6928	Remote Similarity	NPD3122	Phase 3
0.6923	Remote Similarity	NPD7313	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