NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.15
Volume:	249.128
LogP:	4.726
LogD:	3.998
LogS:	-4.483
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.744
Synthetic Accessibility Score:	3.421
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
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:	1.7069456589524634e-05
Pgp-inhibitor:	0.923
Pgp-substrate:	0.116
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.826
Plasma Protein Binding (PPB):	94.6390609741211%
Volume Distribution (VD):	3.353
Pgp-substrate:	7.511817455291748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.858
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.761
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.747
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.487
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.501
CYP3A4-substrate:	0.607

ADMET: Excretion

Clearance (CL):	15.411
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.333
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.914
Carcinogencity:	0.157
Eye Corrosion:	0.068
Eye Irritation:	0.706
Respiratory Toxicity:	0.758

Download Data

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

Natural Product: NPC21594

Natural Product ID:	NPC21594
*Common Name:**	7-Hydroxy-4Alphah-3,4-Dihydrocadalene
IUPAC Name:	(5S)-3,8-dimethyl-5-propan-2-yl-5,6-dihydronaphthalen-2-ol
Synonyms:
Standard InCHIKey:	YZHICMXANUYYLB-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C15H20O/c1-9(2)12-6-5-10(3)13-8-15(16)11(4)7-14(12)13/h5,7-9,12,16H,6H2,1-4H3/t12-/m0/s1
SMILES:	CC(C)[C@@H]1CC=C(C)c2cc(c(C)cc12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452210
PubChem CID:	10220037
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
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473412]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26566007]
NPO25769	Heterotheca inuloides	Species	Asteraceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	31.58	%	PMID[511535]

☑ 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 NPC21594 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	344
0.1-0.2	1904
0.2-0.3	4788
0.3-0.4	12761
0.4-0.5	7118
0.5-0.6	9176
0.6-0.7	4997
0.7-0.8	1251
0.8-0.85	236
0.85-0.9	95
0.9-0.95	23
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.97	High Similarity	NPC151477
0.951	High Similarity	NPC58865
0.95	High Similarity	NPC117115
0.9423	High Similarity	NPC250323
0.9327	High Similarity	NPC176279
0.9327	High Similarity	NPC151537
0.9327	High Similarity	NPC260323
0.9231	High Similarity	NPC13482
0.9151	High Similarity	NPC715
0.91	High Similarity	NPC211885
0.9091	High Similarity	NPC77492
0.9091	High Similarity	NPC79241
0.9091	High Similarity	NPC6597
0.9074	High Similarity	NPC471668
0.9065	High Similarity	NPC195922
0.9057	High Similarity	NPC46940
0.9057	High Similarity	NPC471179
0.9048	High Similarity	NPC141782
0.9048	High Similarity	NPC132720
0.902	High Similarity	NPC238696
0.902	High Similarity	NPC272029
0.8991	High Similarity	NPC477136
0.899	High Similarity	NPC259512
0.899	High Similarity	NPC312132
0.8981	High Similarity	NPC192948
0.8981	High Similarity	NPC35797
0.8962	High Similarity	NPC95716
0.8952	High Similarity	NPC314187
0.8911	High Similarity	NPC72729
0.8909	High Similarity	NPC154030
0.8899	High Similarity	NPC38893
0.8899	High Similarity	NPC477137
0.8899	High Similarity	NPC308311
0.8889	High Similarity	NPC8392
0.8868	High Similarity	NPC224870
0.8857	High Similarity	NPC11554
0.8829	High Similarity	NPC93071
0.8818	High Similarity	NPC304510
0.8818	High Similarity	NPC172219
0.8812	High Similarity	NPC122005
0.8812	High Similarity	NPC299762
0.8812	High Similarity	NPC252821
0.8812	High Similarity	NPC33675
0.8796	High Similarity	NPC263753
0.8788	High Similarity	NPC245187
0.8785	High Similarity	NPC469912
0.8739	High Similarity	NPC471671
0.8727	High Similarity	NPC219112
0.8725	High Similarity	NPC225506
0.8716	High Similarity	NPC268160
0.87	High Similarity	NPC144682
0.87	High Similarity	NPC222146
0.8692	High Similarity	NPC296683
0.8673	High Similarity	NPC259703
0.8673	High Similarity	NPC32322
0.8667	High Similarity	NPC271274
0.8661	High Similarity	NPC126002
0.8661	High Similarity	NPC469644
0.8661	High Similarity	NPC151197
0.8654	High Similarity	NPC475225
0.8641	High Similarity	NPC252105
0.8636	High Similarity	NPC147179
0.8624	High Similarity	NPC322239
0.8624	High Similarity	NPC317869
0.8611	High Similarity	NPC266937
0.8611	High Similarity	NPC470770
0.8611	High Similarity	NPC322753
0.8611	High Similarity	NPC470723
0.8598	High Similarity	NPC299568
0.8598	High Similarity	NPC186385
0.8596	High Similarity	NPC154696
0.8586	High Similarity	NPC304541
0.8586	High Similarity	NPC231150
0.8586	High Similarity	NPC204210
0.8584	High Similarity	NPC478121
0.8571	High Similarity	NPC70436
0.8571	High Similarity	NPC138942
0.8559	High Similarity	NPC308828
0.8559	High Similarity	NPC469663
0.8559	High Similarity	NPC92
0.8558	High Similarity	NPC471228
0.8558	High Similarity	NPC168829
0.8558	High Similarity	NPC269212
0.8558	High Similarity	NPC235762
0.8545	High Similarity	NPC107240
0.8532	High Similarity	NPC62867
0.8532	High Similarity	NPC177962
0.8532	High Similarity	NPC228425
0.8532	High Similarity	NPC302371
0.8529	High Similarity	NPC156313
0.8529	High Similarity	NPC32674
0.8522	High Similarity	NPC282577
0.8509	High Similarity	NPC241001
0.8505	High Similarity	NPC64586
0.8491	Intermediate Similarity	NPC54765
0.8482	Intermediate Similarity	NPC299180
0.8482	Intermediate Similarity	NPC16030
0.8476	Intermediate Similarity	NPC288411
0.8476	Intermediate Similarity	NPC475580
0.8469	Intermediate Similarity	NPC19680
0.8468	Intermediate Similarity	NPC469719
0.8462	Intermediate Similarity	NPC477685
0.8455	Intermediate Similarity	NPC117846
0.8448	Intermediate Similarity	NPC273683
0.8447	Intermediate Similarity	NPC128723
0.844	Intermediate Similarity	NPC77772
0.8435	Intermediate Similarity	NPC249340
0.8435	Intermediate Similarity	NPC162935
0.8435	Intermediate Similarity	NPC474115
0.8431	Intermediate Similarity	NPC202986
0.8416	Intermediate Similarity	NPC152415
0.8416	Intermediate Similarity	NPC316301
0.8416	Intermediate Similarity	NPC289769
0.8416	Intermediate Similarity	NPC27323
0.8411	Intermediate Similarity	NPC66834
0.8411	Intermediate Similarity	NPC320439
0.8407	Intermediate Similarity	NPC469609
0.8396	Intermediate Similarity	NPC47284
0.8384	Intermediate Similarity	NPC258219
0.8384	Intermediate Similarity	NPC242240
0.8384	Intermediate Similarity	NPC318325
0.8384	Intermediate Similarity	NPC123273
0.8381	Intermediate Similarity	NPC108497
0.8378	Intermediate Similarity	NPC249270
0.8376	Intermediate Similarity	NPC199273
0.8365	Intermediate Similarity	NPC174911
0.8364	Intermediate Similarity	NPC473521
0.8362	Intermediate Similarity	NPC11250
0.8362	Intermediate Similarity	NPC121168
0.8362	Intermediate Similarity	NPC297057
0.835	Intermediate Similarity	NPC225464
0.8348	Intermediate Similarity	NPC129176
0.8333	Intermediate Similarity	NPC176893
0.8333	Intermediate Similarity	NPC274678
0.8333	Intermediate Similarity	NPC95344
0.8318	Intermediate Similarity	NPC53740
0.8318	Intermediate Similarity	NPC310456
0.8318	Intermediate Similarity	NPC469913
0.8318	Intermediate Similarity	NPC155072
0.8317	Intermediate Similarity	NPC306884
0.8317	Intermediate Similarity	NPC94139
0.8317	Intermediate Similarity	NPC147284
0.8317	Intermediate Similarity	NPC55903
0.8317	Intermediate Similarity	NPC162314
0.8317	Intermediate Similarity	NPC3358
0.8317	Intermediate Similarity	NPC210497
0.8305	Intermediate Similarity	NPC123506
0.8304	Intermediate Similarity	NPC246760
0.8304	Intermediate Similarity	NPC84999
0.8304	Intermediate Similarity	NPC474486
0.8302	Intermediate Similarity	NPC254965
0.8302	Intermediate Similarity	NPC227458
0.8302	Intermediate Similarity	NPC244513
0.8302	Intermediate Similarity	NPC218879
0.8302	Intermediate Similarity	NPC327811
0.83	Intermediate Similarity	NPC192
0.8291	Intermediate Similarity	NPC471187
0.8288	Intermediate Similarity	NPC319803
0.8288	Intermediate Similarity	NPC321589
0.8286	Intermediate Similarity	NPC51015
0.8286	Intermediate Similarity	NPC12221
0.8283	Intermediate Similarity	NPC113460
0.8283	Intermediate Similarity	NPC25493
0.8283	Intermediate Similarity	NPC27974
0.8273	Intermediate Similarity	NPC476632
0.8273	Intermediate Similarity	NPC54373
0.8273	Intermediate Similarity	NPC165770
0.8273	Intermediate Similarity	NPC4493
0.8273	Intermediate Similarity	NPC224527
0.8273	Intermediate Similarity	NPC225679
0.8269	Intermediate Similarity	NPC92730
0.8261	Intermediate Similarity	NPC135467
0.8261	Intermediate Similarity	NPC260832
0.8252	Intermediate Similarity	NPC132271
0.8252	Intermediate Similarity	NPC292730
0.8252	Intermediate Similarity	NPC216520
0.8252	Intermediate Similarity	NPC82664
0.8252	Intermediate Similarity	NPC473388
0.8246	Intermediate Similarity	NPC206
0.8246	Intermediate Similarity	NPC328694
0.8241	Intermediate Similarity	NPC228737
0.8235	Intermediate Similarity	NPC76938
0.8235	Intermediate Similarity	NPC128062
0.823	Intermediate Similarity	NPC474387
0.823	Intermediate Similarity	NPC247858
0.823	Intermediate Similarity	NPC115808
0.823	Intermediate Similarity	NPC154511
0.823	Intermediate Similarity	NPC474358
0.823	Intermediate Similarity	NPC312105
0.823	Intermediate Similarity	NPC257540
0.823	Intermediate Similarity	NPC137496
0.823	Intermediate Similarity	NPC141001
0.8224	Intermediate Similarity	NPC219286
0.8224	Intermediate Similarity	NPC37802
0.8224	Intermediate Similarity	NPC99557
0.822	Intermediate Similarity	NPC181334
0.8218	Intermediate Similarity	NPC306074
0.8218	Intermediate Similarity	NPC155908
0.8214	Intermediate Similarity	NPC471534
0.8208	Intermediate Similarity	NPC168393

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 NPC21594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	1028
0.2-0.3	1392
0.3-0.4	2987
0.4-0.5	1803
0.5-0.6	1105
0.6-0.7	372
0.7-0.8	80
0.8-0.85	12
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.899	High Similarity	NPD288	Approved
0.8889	High Similarity	NPD844	Approved
0.8704	High Similarity	NPD7635	Approved
0.87	High Similarity	NPD1809	Phase 2
0.8687	High Similarity	NPD845	Approved
0.8598	High Similarity	NPD4750	Phase 3
0.8585	High Similarity	NPD2342	Discontinued
0.8447	Intermediate Similarity	NPD3020	Approved
0.8416	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD2860	Approved
0.8155	Intermediate Similarity	NPD2859	Approved
0.8103	Intermediate Similarity	NPD2932	Approved
0.8091	Intermediate Similarity	NPD3021	Approved
0.8091	Intermediate Similarity	NPD3022	Approved
0.8087	Intermediate Similarity	NPD3091	Approved
0.8058	Intermediate Similarity	NPD2933	Approved
0.8058	Intermediate Similarity	NPD2934	Approved
0.7983	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD4626	Approved
0.7949	Intermediate Similarity	NPD1751	Approved
0.7949	Intermediate Similarity	NPD3019	Approved
0.7949	Intermediate Similarity	NPD4059	Approved
0.7944	Intermediate Similarity	NPD846	Approved
0.7944	Intermediate Similarity	NPD940	Approved
0.7928	Intermediate Similarity	NPD1792	Phase 2
0.7879	Intermediate Similarity	NPD111	Approved
0.7863	Intermediate Similarity	NPD4093	Discontinued
0.7818	Intermediate Similarity	NPD1444	Approved
0.7818	Intermediate Similarity	NPD1445	Approved
0.7815	Intermediate Similarity	NPD3092	Approved
0.7797	Intermediate Similarity	NPD2286	Discontinued
0.7759	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD497	Approved
0.7652	Intermediate Similarity	NPD498	Approved
0.7652	Intermediate Similarity	NPD496	Approved
0.7652	Intermediate Similarity	NPD495	Approved
0.7652	Intermediate Similarity	NPD1398	Phase 1
0.7647	Intermediate Similarity	NPD3095	Discontinued
0.7632	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5304	Approved
0.7627	Intermediate Similarity	NPD5303	Approved
0.7607	Intermediate Similarity	NPD7340	Approved
0.7563	Intermediate Similarity	NPD5691	Approved
0.7561	Intermediate Similarity	NPD3094	Phase 2
0.7545	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD9500	Approved
0.7541	Intermediate Similarity	NPD4749	Approved
0.7523	Intermediate Similarity	NPD1242	Phase 1
0.75	Intermediate Similarity	NPD4589	Approved
0.75	Intermediate Similarity	NPD2195	Approved
0.75	Intermediate Similarity	NPD2229	Approved
0.75	Intermediate Similarity	NPD2228	Approved
0.75	Intermediate Similarity	NPD2234	Approved
0.75	Intermediate Similarity	NPD2194	Approved
0.75	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD6696	Suspended
0.748	Intermediate Similarity	NPD1283	Approved
0.7479	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4625	Phase 3
0.7442	Intermediate Similarity	NPD4097	Suspended
0.744	Intermediate Similarity	NPD5736	Approved
0.744	Intermediate Similarity	NPD3635	Approved
0.744	Intermediate Similarity	NPD3637	Approved
0.744	Intermediate Similarity	NPD3636	Approved
0.7422	Intermediate Similarity	NPD4060	Phase 1
0.7417	Intermediate Similarity	NPD1651	Approved
0.7381	Intermediate Similarity	NPD2606	Approved
0.7381	Intermediate Similarity	NPD2605	Approved
0.7377	Intermediate Similarity	NPD1201	Approved
0.7373	Intermediate Similarity	NPD6671	Approved
0.7323	Intermediate Similarity	NPD5155	Approved
0.7323	Intermediate Similarity	NPD5156	Approved
0.7311	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD3023	Approved
0.7295	Intermediate Similarity	NPD3026	Approved
0.7273	Intermediate Similarity	NPD3024	Approved
0.7273	Intermediate Similarity	NPD3025	Approved
0.7266	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3594	Approved
0.7244	Intermediate Similarity	NPD3595	Approved
0.7236	Intermediate Similarity	NPD1281	Approved
0.7222	Intermediate Similarity	NPD4624	Approved
0.7209	Intermediate Similarity	NPD6663	Approved
0.7203	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD228	Approved
0.7168	Intermediate Similarity	NPD9610	Approved
0.7168	Intermediate Similarity	NPD9608	Approved
0.7154	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD1793	Approved
0.7143	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1791	Approved
0.7131	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1669	Approved
0.7097	Intermediate Similarity	NPD1611	Approved
0.7083	Intermediate Similarity	NPD709	Approved
0.7068	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5283	Phase 1
0.7054	Intermediate Similarity	NPD3028	Approved
0.7049	Intermediate Similarity	NPD7330	Discontinued
0.704	Intermediate Similarity	NPD2232	Approved
0.704	Intermediate Similarity	NPD2233	Approved
0.704	Intermediate Similarity	NPD2230	Approved
0.7031	Intermediate Similarity	NPD2861	Phase 2
0.7025	Intermediate Similarity	NPD7636	Approved
0.7016	Intermediate Similarity	NPD3143	Discontinued
0.7016	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5405	Approved
0.7015	Intermediate Similarity	NPD5406	Approved
0.7015	Intermediate Similarity	NPD5404	Approved
0.7015	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5327	Phase 3
0.6975	Remote Similarity	NPD9377	Approved
0.6975	Remote Similarity	NPD9379	Approved
0.696	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1610	Phase 2
0.696	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7742	Approved
0.694	Remote Similarity	NPD7743	Approved
0.6917	Remote Similarity	NPD2157	Approved
0.6906	Remote Similarity	NPD7390	Discontinued
0.6905	Remote Similarity	NPD3070	Discontinued
0.6894	Remote Similarity	NPD4140	Approved
0.688	Remote Similarity	NPD1981	Approved
0.688	Remote Similarity	NPD1980	Approved
0.688	Remote Similarity	NPD1983	Approved
0.6875	Remote Similarity	NPD9273	Approved
0.6875	Remote Similarity	NPD1164	Approved
0.687	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2209	Approved
0.6861	Remote Similarity	NPD2211	Approved
0.6861	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.686	Remote Similarity	NPD475	Phase 2
0.6857	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4908	Phase 1
0.6842	Remote Similarity	NPD5735	Approved
0.6838	Remote Similarity	NPD4725	Approved
0.6838	Remote Similarity	NPD4721	Approved
0.6838	Remote Similarity	NPD4726	Approved
0.6833	Remote Similarity	NPD1138	Approved
0.6829	Remote Similarity	NPD7644	Approved
0.6812	Remote Similarity	NPD7003	Approved
0.68	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2668	Approved
0.68	Remote Similarity	NPD2667	Approved
0.6791	Remote Similarity	NPD6353	Approved
0.6788	Remote Similarity	NPD4257	Approved
0.6788	Remote Similarity	NPD4256	Phase 2
0.6786	Remote Similarity	NPD2421	Approved
0.6786	Remote Similarity	NPD2420	Approved
0.6786	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7041	Phase 2
0.678	Remote Similarity	NPD2684	Approved
0.6769	Remote Similarity	NPD4208	Discontinued
0.6769	Remote Similarity	NPD1712	Approved
0.6768	Remote Similarity	NPD9087	Approved
0.6767	Remote Similarity	NPD2979	Phase 3
0.6765	Remote Similarity	NPD6099	Approved
0.6765	Remote Similarity	NPD6100	Approved
0.6754	Remote Similarity	NPD1616	Discontinued
0.675	Remote Similarity	NPD1137	Approved
0.675	Remote Similarity	NPD1139	Approved
0.6744	Remote Similarity	NPD1135	Approved
0.6744	Remote Similarity	NPD1131	Approved
0.6744	Remote Similarity	NPD1129	Approved
0.6744	Remote Similarity	NPD1134	Approved
0.6744	Remote Similarity	NPD1133	Approved
0.6742	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1039	Discontinued
0.6739	Remote Similarity	NPD3638	Discontinued
0.6723	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD9614	Approved
0.6721	Remote Similarity	NPD9618	Approved
0.6719	Remote Similarity	NPD1755	Approved
0.6692	Remote Similarity	NPD6584	Phase 3
0.6691	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD8166	Discontinued
0.669	Remote Similarity	NPD6090	Discontinued
0.6667	Remote Similarity	NPD6387	Discontinued
0.6667	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD8651	Approved
0.6667	Remote Similarity	NPD7037	Approved
0.6667	Remote Similarity	NPD7157	Approved
0.6667	Remote Similarity	NPD255	Approved
0.6643	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2238	Phase 2
0.6642	Remote Similarity	NPD2935	Discontinued
0.6642	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4212	Discontinued

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