NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.17
Volume:	286.641
LogP:	3.246
LogD:	2.971
LogS:	-4.41
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.863
Synthetic Accessibility Score:	3.868
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.444
MDCK Permeability:	1.5525029084528796e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.778
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.934
30% Bioavailability (F30%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	90.00550079345703%
Volume Distribution (VD):	1.045
Pgp-substrate:	6.899094581604004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.755
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.595
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.71

ADMET: Excretion

Clearance (CL):	9.338
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.061
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.207
Skin Sensitization:	0.058
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.056

Download Data

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

Natural Product: NPC470724

Natural Product ID:	NPC470724
*Common Name:**	(1R)-7-Methoxy-1,6-Dimethyl-4-Propan-2-Yl-3,4-Dihydro-2H-Naphthalene-1,2-Diol
IUPAC Name:	(1R)-7-methoxy-1,6-dimethyl-4-propan-2-yl-3,4-dihydro-2H-naphthalene-1,2-diol
Synonyms:
Standard InCHIKey:	SEGVFKZPKBQZRQ-QJLPXFQTSA-N
Standard InCHI:	InChI=1S/C16H24O3/c1-9(2)11-7-15(17)16(4,18)13-8-14(19-5)10(3)6-12(11)13/h6,8-9,11,15,17-18H,7H2,1-5H3/t11?,15?,16-/m1/s1
SMILES:	COc1cc2c(cc1C)C(CC([C@]2(C)O)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2206799
PubChem CID:	71455987
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	>	50000.0	nM	PMID[490599]

☑ 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 NPC470724 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	359
0.1-0.2	1430
0.2-0.3	3610
0.3-0.4	9881
0.4-0.5	9187
0.5-0.6	5019
0.6-0.7	9446
0.7-0.8	3333
0.8-0.85	400
0.85-0.9	29
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC470726
0.9675	High Similarity	NPC470727
0.8968	High Similarity	NPC186889
0.8968	High Similarity	NPC471077
0.8931	High Similarity	NPC68292
0.8906	High Similarity	NPC196193
0.8871	High Similarity	NPC152946
0.8846	High Similarity	NPC227719
0.881	High Similarity	NPC4286
0.881	High Similarity	NPC76119
0.8788	High Similarity	NPC327735
0.8788	High Similarity	NPC472800
0.8779	High Similarity	NPC311256
0.876	High Similarity	NPC143483
0.875	High Similarity	NPC472968
0.8741	High Similarity	NPC186033
0.871	High Similarity	NPC129176
0.8692	High Similarity	NPC312341
0.8692	High Similarity	NPC78575
0.8661	High Similarity	NPC124030
0.8661	High Similarity	NPC105031
0.8661	High Similarity	NPC293801
0.8647	High Similarity	NPC126101
0.8636	High Similarity	NPC16485
0.8626	High Similarity	NPC18842
0.8626	High Similarity	NPC59239
0.8626	High Similarity	NPC228843
0.8615	High Similarity	NPC99795
0.8605	High Similarity	NPC223912
0.8561	High Similarity	NPC26394
0.8548	High Similarity	NPC469644
0.8538	High Similarity	NPC472797
0.8529	High Similarity	NPC265075
0.8527	High Similarity	NPC5428
0.8527	High Similarity	NPC118533
0.8527	High Similarity	NPC21563
0.8527	High Similarity	NPC469386
0.8527	High Similarity	NPC165045
0.8519	High Similarity	NPC6300
0.8519	High Similarity	NPC184613
0.8519	High Similarity	NPC230124
0.8519	High Similarity	NPC114171
0.8516	High Similarity	NPC81641
0.8516	High Similarity	NPC148627
0.8507	High Similarity	NPC263367
0.8507	High Similarity	NPC10737
0.8507	High Similarity	NPC54743
0.8507	High Similarity	NPC177160
0.8507	High Similarity	NPC209985
0.8507	High Similarity	NPC156502
0.8507	High Similarity	NPC29799
0.8507	High Similarity	NPC477939
0.85	High Similarity	NPC470723
0.8496	Intermediate Similarity	NPC193026
0.8496	Intermediate Similarity	NPC49603
0.8496	Intermediate Similarity	NPC187616
0.8496	Intermediate Similarity	NPC471942
0.8485	Intermediate Similarity	NPC230219
0.8485	Intermediate Similarity	NPC472798
0.8473	Intermediate Similarity	NPC11089
0.8468	Intermediate Similarity	NPC471671
0.8462	Intermediate Similarity	NPC470084
0.8462	Intermediate Similarity	NPC307050
0.8462	Intermediate Similarity	NPC277458
0.8462	Intermediate Similarity	NPC201069
0.845	Intermediate Similarity	NPC82299
0.8444	Intermediate Similarity	NPC156948
0.8444	Intermediate Similarity	NPC301765
0.8444	Intermediate Similarity	NPC86605
0.8444	Intermediate Similarity	NPC3072
0.8444	Intermediate Similarity	NPC46277
0.8433	Intermediate Similarity	NPC256262
0.8429	Intermediate Similarity	NPC474397
0.8425	Intermediate Similarity	NPC57199
0.8425	Intermediate Similarity	NPC150026
0.8421	Intermediate Similarity	NPC170185
0.8417	Intermediate Similarity	NPC132720
0.8417	Intermediate Similarity	NPC221318
0.8409	Intermediate Similarity	NPC15543
0.8409	Intermediate Similarity	NPC160623
0.8409	Intermediate Similarity	NPC277804
0.8397	Intermediate Similarity	NPC472796
0.8397	Intermediate Similarity	NPC472795
0.8387	Intermediate Similarity	NPC304510
0.8387	Intermediate Similarity	NPC172219
0.8385	Intermediate Similarity	NPC473221
0.8382	Intermediate Similarity	NPC32630
0.837	Intermediate Similarity	NPC133025
0.8359	Intermediate Similarity	NPC471693
0.8359	Intermediate Similarity	NPC474160
0.8358	Intermediate Similarity	NPC209199
0.8357	Intermediate Similarity	NPC233980
0.8346	Intermediate Similarity	NPC474115
0.8346	Intermediate Similarity	NPC85595
0.8346	Intermediate Similarity	NPC303144
0.8346	Intermediate Similarity	NPC48623
0.8346	Intermediate Similarity	NPC168707
0.8345	Intermediate Similarity	NPC473845
0.8345	Intermediate Similarity	NPC164183
0.8333	Intermediate Similarity	NPC174495
0.8333	Intermediate Similarity	NPC242807
0.8333	Intermediate Similarity	NPC92164
0.8333	Intermediate Similarity	NPC103916
0.8333	Intermediate Similarity	NPC470725
0.8333	Intermediate Similarity	NPC257582
0.8333	Intermediate Similarity	NPC42300
0.8333	Intermediate Similarity	NPC135467
0.8333	Intermediate Similarity	NPC260832
0.8333	Intermediate Similarity	NPC64201
0.8333	Intermediate Similarity	NPC187998
0.8333	Intermediate Similarity	NPC153739
0.8333	Intermediate Similarity	NPC470917
0.8333	Intermediate Similarity	NPC145305
0.8333	Intermediate Similarity	NPC241522
0.8333	Intermediate Similarity	NPC77040
0.8321	Intermediate Similarity	NPC211179
0.8321	Intermediate Similarity	NPC215300
0.8321	Intermediate Similarity	NPC45774
0.8321	Intermediate Similarity	NPC184733
0.8321	Intermediate Similarity	NPC11258
0.8321	Intermediate Similarity	NPC21867
0.8321	Intermediate Similarity	NPC128208
0.8321	Intermediate Similarity	NPC38017
0.8321	Intermediate Similarity	NPC12668
0.8321	Intermediate Similarity	NPC308768
0.8321	Intermediate Similarity	NPC282703
0.8321	Intermediate Similarity	NPC129570
0.8321	Intermediate Similarity	NPC23012
0.8321	Intermediate Similarity	NPC38604
0.832	Intermediate Similarity	NPC154030
0.832	Intermediate Similarity	NPC469609
0.8309	Intermediate Similarity	NPC6100
0.8309	Intermediate Similarity	NPC477938
0.8309	Intermediate Similarity	NPC56329
0.8309	Intermediate Similarity	NPC242715
0.8309	Intermediate Similarity	NPC266006
0.8309	Intermediate Similarity	NPC470722
0.8309	Intermediate Similarity	NPC22902
0.8309	Intermediate Similarity	NPC156888
0.8309	Intermediate Similarity	NPC470721
0.8308	Intermediate Similarity	NPC170485
0.8308	Intermediate Similarity	NPC206882
0.8306	Intermediate Similarity	NPC38893
0.8306	Intermediate Similarity	NPC477137
0.8306	Intermediate Similarity	NPC312105
0.8306	Intermediate Similarity	NPC308311
0.8296	Intermediate Similarity	NPC214853
0.8296	Intermediate Similarity	NPC55239
0.8296	Intermediate Similarity	NPC180602
0.8296	Intermediate Similarity	NPC313081
0.8296	Intermediate Similarity	NPC240279
0.8295	Intermediate Similarity	NPC109822
0.8295	Intermediate Similarity	NPC94276
0.8293	Intermediate Similarity	NPC470837
0.8286	Intermediate Similarity	NPC472457
0.8281	Intermediate Similarity	NPC18128
0.8281	Intermediate Similarity	NPC471794
0.8281	Intermediate Similarity	NPC204535
0.8281	Intermediate Similarity	NPC46586
0.8281	Intermediate Similarity	NPC85488
0.8281	Intermediate Similarity	NPC77789
0.8281	Intermediate Similarity	NPC30462
0.8281	Intermediate Similarity	NPC188997
0.8273	Intermediate Similarity	NPC258083
0.8271	Intermediate Similarity	NPC474017
0.8268	Intermediate Similarity	NPC102639
0.8268	Intermediate Similarity	NPC45663
0.8261	Intermediate Similarity	NPC87725
0.8261	Intermediate Similarity	NPC71046
0.8261	Intermediate Similarity	NPC471414
0.8261	Intermediate Similarity	NPC263261
0.8258	Intermediate Similarity	NPC475875
0.8254	Intermediate Similarity	NPC151197
0.8254	Intermediate Similarity	NPC135961
0.8252	Intermediate Similarity	NPC158784
0.8248	Intermediate Similarity	NPC105847
0.8248	Intermediate Similarity	NPC275061
0.8248	Intermediate Similarity	NPC220344
0.8248	Intermediate Similarity	NPC243996
0.8248	Intermediate Similarity	NPC243759
0.8248	Intermediate Similarity	NPC132804
0.8248	Intermediate Similarity	NPC471183
0.8248	Intermediate Similarity	NPC218131
0.8244	Intermediate Similarity	NPC242032
0.8244	Intermediate Similarity	NPC98745
0.8244	Intermediate Similarity	NPC53781
0.8244	Intermediate Similarity	NPC106511
0.824	Intermediate Similarity	NPC477136
0.824	Intermediate Similarity	NPC25648
0.8235	Intermediate Similarity	NPC143139
0.8235	Intermediate Similarity	NPC470802
0.8235	Intermediate Similarity	NPC202846
0.8235	Intermediate Similarity	NPC30632
0.8235	Intermediate Similarity	NPC234952
0.8231	Intermediate Similarity	NPC228771
0.8231	Intermediate Similarity	NPC105718
0.8231	Intermediate Similarity	NPC476254
0.8231	Intermediate Similarity	NPC131397
0.8231	Intermediate Similarity	NPC266705
0.8231	Intermediate Similarity	NPC29008

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 NPC470724 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	891
0.2-0.3	1807
0.3-0.4	2719
0.4-0.5	1682
0.5-0.6	953
0.6-0.7	651
0.7-0.8	115
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
0.8394	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD3620	Phase 2
0.8189	Intermediate Similarity	NPD4626	Approved
0.8154	Intermediate Similarity	NPD6696	Suspended
0.8129	Intermediate Similarity	NPD6674	Discontinued
0.812	Intermediate Similarity	NPD3027	Phase 3
0.812	Intermediate Similarity	NPD4625	Phase 3
0.8106	Intermediate Similarity	NPD2861	Phase 2
0.8074	Intermediate Similarity	NPD4060	Phase 1
0.806	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD5735	Approved
0.7969	Intermediate Similarity	NPD5691	Approved
0.7941	Intermediate Similarity	NPD2238	Phase 2
0.7939	Intermediate Similarity	NPD4749	Approved
0.7874	Intermediate Similarity	NPD7340	Approved
0.7857	Intermediate Similarity	NPD5763	Approved
0.7857	Intermediate Similarity	NPD5762	Approved
0.7826	Intermediate Similarity	NPD4097	Suspended
0.781	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1613	Approved
0.7794	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD3092	Approved
0.7778	Intermediate Similarity	NPD5283	Phase 1
0.7778	Intermediate Similarity	NPD1398	Phase 1
0.7761	Intermediate Similarity	NPD4624	Approved
0.7744	Intermediate Similarity	NPD8651	Approved
0.7744	Intermediate Similarity	NPD1283	Approved
0.7727	Intermediate Similarity	NPD2232	Approved
0.7727	Intermediate Similarity	NPD2233	Approved
0.7727	Intermediate Similarity	NPD2230	Approved
0.7698	Intermediate Similarity	NPD7635	Approved
0.7692	Intermediate Similarity	NPD1651	Approved
0.7687	Intermediate Similarity	NPD3094	Phase 2
0.7681	Intermediate Similarity	NPD4140	Approved
0.7669	Intermediate Similarity	NPD5327	Phase 3
0.7661	Intermediate Similarity	NPD2684	Approved
0.7656	Intermediate Similarity	NPD6671	Approved
0.7652	Intermediate Similarity	NPD1610	Phase 2
0.7652	Intermediate Similarity	NPD3705	Approved
0.7647	Intermediate Similarity	NPD4908	Phase 1
0.7639	Intermediate Similarity	NPD2677	Approved
0.7619	Intermediate Similarity	NPD228	Approved
0.7615	Intermediate Similarity	NPD3091	Approved
0.76	Intermediate Similarity	NPD37	Approved
0.7574	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6353	Approved
0.7519	Intermediate Similarity	NPD1281	Approved
0.7519	Intermediate Similarity	NPD7157	Approved
0.7518	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD3021	Approved
0.746	Intermediate Similarity	NPD4750	Phase 3
0.746	Intermediate Similarity	NPD3022	Approved
0.7451	Intermediate Similarity	NPD4966	Approved
0.7451	Intermediate Similarity	NPD4965	Approved
0.7451	Intermediate Similarity	NPD4967	Phase 2
0.744	Intermediate Similarity	NPD290	Approved
0.7432	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2979	Phase 3
0.7422	Intermediate Similarity	NPD7843	Approved
0.7413	Intermediate Similarity	NPD6099	Approved
0.7413	Intermediate Similarity	NPD6100	Approved
0.741	Intermediate Similarity	NPD7985	Registered
0.7407	Intermediate Similarity	NPD1669	Approved
0.7394	Intermediate Similarity	NPD4536	Approved
0.7394	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4538	Approved
0.7388	Intermediate Similarity	NPD1611	Approved
0.7388	Intermediate Similarity	NPD1091	Approved
0.7376	Intermediate Similarity	NPD3657	Discovery
0.7368	Intermediate Similarity	NPD2668	Approved
0.7368	Intermediate Similarity	NPD2667	Approved
0.7368	Intermediate Similarity	NPD3095	Discontinued
0.7368	Intermediate Similarity	NPD5125	Phase 3
0.7368	Intermediate Similarity	NPD5126	Approved
0.7365	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6234	Discontinued
0.7348	Intermediate Similarity	NPD1548	Phase 1
0.7333	Intermediate Similarity	NPD2235	Phase 2
0.7333	Intermediate Similarity	NPD2231	Phase 2
0.7329	Intermediate Similarity	NPD4628	Phase 3
0.7324	Intermediate Similarity	NPD2157	Approved
0.7308	Intermediate Similarity	NPD4666	Phase 3
0.7302	Intermediate Similarity	NPD2342	Discontinued
0.7297	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7041	Phase 2
0.7295	Intermediate Similarity	NPD3020	Approved
0.7293	Intermediate Similarity	NPD1357	Approved
0.7292	Intermediate Similarity	NPD2438	Suspended
0.7278	Intermediate Similarity	NPD2970	Approved
0.7278	Intermediate Similarity	NPD2969	Approved
0.7273	Intermediate Similarity	NPD7644	Approved
0.7273	Intermediate Similarity	NPD288	Approved
0.7254	Intermediate Similarity	NPD5124	Phase 1
0.7254	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6355	Discontinued
0.7252	Intermediate Similarity	NPD709	Approved
0.7244	Intermediate Similarity	NPD5709	Phase 3
0.7239	Intermediate Similarity	NPD1778	Approved
0.7231	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5058	Phase 3
0.723	Intermediate Similarity	NPD6666	Approved
0.723	Intermediate Similarity	NPD6667	Approved
0.7222	Intermediate Similarity	NPD5960	Phase 3
0.7222	Intermediate Similarity	NPD5588	Approved
0.7215	Intermediate Similarity	NPD3051	Approved
0.7211	Intermediate Similarity	NPD7003	Approved
0.7208	Intermediate Similarity	NPD5929	Approved
0.7208	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5844	Phase 1
0.72	Intermediate Similarity	NPD6090	Discontinued
0.7194	Intermediate Similarity	NPD3018	Phase 2
0.7192	Intermediate Similarity	NPD2424	Discontinued
0.719	Intermediate Similarity	NPD844	Approved
0.7163	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD5177	Phase 3
0.7133	Intermediate Similarity	NPD2534	Approved
0.7133	Intermediate Similarity	NPD2533	Approved
0.7133	Intermediate Similarity	NPD2532	Approved
0.7133	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2489	Approved
0.7125	Intermediate Similarity	NPD27	Approved
0.7123	Intermediate Similarity	NPD6004	Phase 3
0.7123	Intermediate Similarity	NPD6002	Phase 3
0.7123	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6005	Phase 3
0.7123	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6584	Phase 3
0.7122	Intermediate Similarity	NPD3691	Phase 2
0.7122	Intermediate Similarity	NPD3690	Phase 2
0.712	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6516	Phase 2
0.7111	Intermediate Similarity	NPD5846	Approved
0.7111	Intermediate Similarity	NPD4059	Approved
0.7107	Intermediate Similarity	NPD6232	Discontinued
0.7103	Intermediate Similarity	NPD2156	Approved
0.7103	Intermediate Similarity	NPD2154	Approved
0.7103	Intermediate Similarity	NPD4108	Discontinued
0.7103	Intermediate Similarity	NPD2155	Approved
0.7095	Intermediate Similarity	NPD3892	Phase 2
0.7095	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6331	Phase 2
0.7095	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7095	Approved
0.709	Intermediate Similarity	NPD7741	Discontinued
0.7087	Intermediate Similarity	NPD968	Approved
0.7086	Intermediate Similarity	NPD2676	Approved
0.7086	Intermediate Similarity	NPD2675	Approved
0.7083	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7473	Discontinued
0.708	Intermediate Similarity	NPD1608	Approved
0.7075	Intermediate Similarity	NPD7037	Approved
0.7071	Intermediate Similarity	NPD5736	Approved
0.7071	Intermediate Similarity	NPD1712	Approved
0.7059	Intermediate Similarity	NPD3496	Discontinued
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4477	Approved
0.7055	Intermediate Similarity	NPD2935	Discontinued
0.7055	Intermediate Similarity	NPD4476	Approved
0.7055	Intermediate Similarity	NPD2531	Phase 2
0.7054	Intermediate Similarity	NPD5451	Approved
0.7051	Intermediate Similarity	NPD2563	Approved
0.7051	Intermediate Similarity	NPD2560	Approved
0.7049	Intermediate Similarity	NPD2859	Approved
0.7049	Intermediate Similarity	NPD2860	Approved
0.7049	Intermediate Similarity	NPD1809	Phase 2
0.7047	Intermediate Similarity	NPD5241	Discontinued
0.7044	Intermediate Similarity	NPD6959	Discontinued
0.7042	Intermediate Similarity	NPD5111	Phase 2
0.7042	Intermediate Similarity	NPD5110	Phase 2
0.7042	Intermediate Similarity	NPD6798	Discontinued
0.7042	Intermediate Similarity	NPD5109	Approved
0.7037	Intermediate Similarity	NPD3443	Approved
0.7037	Intermediate Similarity	NPD3445	Approved
0.7037	Intermediate Similarity	NPD3444	Approved
0.7034	Intermediate Similarity	NPD7097	Phase 1
0.7029	Intermediate Similarity	NPD2982	Phase 2
0.7029	Intermediate Similarity	NPD2983	Phase 2
0.7027	Intermediate Similarity	NPD4236	Phase 3
0.7027	Intermediate Similarity	NPD4237	Approved
0.7027	Intermediate Similarity	NPD3060	Approved
0.7025	Intermediate Similarity	NPD845	Approved
0.7023	Intermediate Similarity	NPD1138	Approved
0.702	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4380	Phase 2
0.7	Intermediate Similarity	NPD3122	Phase 3
0.6992	Remote Similarity	NPD6387	Discontinued
0.6986	Remote Similarity	NPD7033	Discontinued
0.6985	Remote Similarity	NPD2932	Approved
0.6985	Remote Similarity	NPD3019	Approved
0.698	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4110	Phase 3
0.6974	Remote Similarity	NPD7314	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data