NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	4.325
LogD:	2.926
LogS:	-3.235
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	3.523
Fsp3:	0.6
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:	-4.73
MDCK Permeability:	1.7246766219614074e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.64
Plasma Protein Binding (PPB):	98.37228393554688%
Volume Distribution (VD):	4.091
Pgp-substrate:	1.668328046798706%

ADMET: Metabolism

CYP1A2-inhibitor:	0.553
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.141
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.549
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.08
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.253
CYP3A4-substrate:	0.596

ADMET: Excretion

Clearance (CL):	10.754
Half-life (T1/2):	0.527

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.113
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.821
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.92
Carcinogencity:	0.226
Eye Corrosion:	0.043
Eye Irritation:	0.922
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC471179

Natural Product ID:	NPC471179
*Common Name:**	(1S,4R)-7,8-Dihydroxycalamenene
IUPAC Name:	(5R,8S)-3,8-dimethyl-5-propan-2-yl-5,6,7,8-tetrahydronaphthalene-1,2-diol
Synonyms:
Standard InCHIKey:	CGMRLDYEJWKTEX-GXSJLCMTSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-8(2)11-6-5-9(3)13-12(11)7-10(4)14(16)15(13)17/h7-9,11,16-17H,5-6H2,1-4H3/t9-,11+/m0/s1
SMILES:	CC([C@H]1CC[C@@H](c2c1cc(C)c(c2O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386327
PubChem CID:	14864211
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
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23734721]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15986	Alangium chinense	Species	Cornaceae	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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3494	Organism	Coxsackievirus	Coxsackievirus	IC50	=	7400.0	nM	PMID[507871]

☑ 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 NPC471179 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	325
0.1-0.2	1795
0.2-0.3	4568
0.3-0.4	13155
0.4-0.5	6620
0.5-0.6	9003
0.6-0.7	5437
0.7-0.8	1596
0.8-0.85	158
0.85-0.9	31
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9533	High Similarity	NPC317869
0.9189	High Similarity	NPC16030
0.9151	High Similarity	NPC151477
0.9057	High Similarity	NPC21594
0.9027	High Similarity	NPC176893
0.8991	High Similarity	NPC151537
0.8981	High Similarity	NPC58865
0.8962	High Similarity	NPC117115
0.8957	High Similarity	NPC474115
0.8889	High Similarity	NPC233835
0.8818	High Similarity	NPC260323
0.8818	High Similarity	NPC176279
0.8807	High Similarity	NPC254833
0.8807	High Similarity	NPC228343
0.8785	High Similarity	NPC239291
0.8739	High Similarity	NPC250323
0.8739	High Similarity	NPC46940
0.8729	High Similarity	NPC224342
0.8727	High Similarity	NPC132720
0.8718	High Similarity	NPC471794
0.8696	High Similarity	NPC191866
0.8692	High Similarity	NPC238696
0.8673	High Similarity	NPC35797
0.8673	High Similarity	NPC192948
0.8661	High Similarity	NPC715
0.8649	High Similarity	NPC95716
0.8632	High Similarity	NPC39029
0.8632	High Similarity	NPC237667
0.8596	High Similarity	NPC38893
0.8596	High Similarity	NPC477137
0.8596	High Similarity	NPC471668
0.8596	High Similarity	NPC308311
0.8595	High Similarity	NPC201069
0.8584	High Similarity	NPC195922
0.8559	High Similarity	NPC13482
0.8559	High Similarity	NPC141782
0.8547	High Similarity	NPC24125
0.8545	High Similarity	NPC11554
0.8532	High Similarity	NPC477814
0.8522	High Similarity	NPC277588
0.8522	High Similarity	NPC477136
0.8522	High Similarity	NPC172219
0.8522	High Similarity	NPC304510
0.8519	High Similarity	NPC471511
0.8519	High Similarity	NPC120719
0.8519	High Similarity	NPC272029
0.8487	Intermediate Similarity	NPC53567
0.8468	Intermediate Similarity	NPC314187
0.8462	Intermediate Similarity	NPC475245
0.8455	Intermediate Similarity	NPC99795
0.8448	Intermediate Similarity	NPC144343
0.8448	Intermediate Similarity	NPC471671
0.8435	Intermediate Similarity	NPC469663
0.8435	Intermediate Similarity	NPC219112
0.8435	Intermediate Similarity	NPC92
0.8426	Intermediate Similarity	NPC196479
0.8421	Intermediate Similarity	NPC268160
0.8411	Intermediate Similarity	NPC211885
0.8411	Intermediate Similarity	NPC72729
0.8403	Intermediate Similarity	NPC321402
0.8396	Intermediate Similarity	NPC79241
0.8396	Intermediate Similarity	NPC6597
0.8396	Intermediate Similarity	NPC109955
0.8396	Intermediate Similarity	NPC77492
0.8393	Intermediate Similarity	NPC224870
0.8387	Intermediate Similarity	NPC312341
0.8387	Intermediate Similarity	NPC78575
0.8387	Intermediate Similarity	NPC291001
0.8376	Intermediate Similarity	NPC151197
0.8376	Intermediate Similarity	NPC126002
0.8376	Intermediate Similarity	NPC469644
0.8376	Intermediate Similarity	NPC93071
0.8376	Intermediate Similarity	NPC217174
0.8361	Intermediate Similarity	NPC476536
0.8348	Intermediate Similarity	NPC472893
0.8348	Intermediate Similarity	NPC147179
0.8348	Intermediate Similarity	NPC469719
0.8333	Intermediate Similarity	NPC471485
0.8333	Intermediate Similarity	NPC263753
0.832	Intermediate Similarity	NPC59239
0.8319	Intermediate Similarity	NPC469912
0.8305	Intermediate Similarity	NPC478121
0.8304	Intermediate Similarity	NPC55617
0.8304	Intermediate Similarity	NPC62258
0.8302	Intermediate Similarity	NPC259512
0.8302	Intermediate Similarity	NPC312132
0.8293	Intermediate Similarity	NPC23012
0.8291	Intermediate Similarity	NPC154030
0.8276	Intermediate Similarity	NPC308828
0.8273	Intermediate Similarity	NPC138942
0.8264	Intermediate Similarity	NPC15127
0.8261	Intermediate Similarity	NPC107240
0.8261	Intermediate Similarity	NPC120280
0.8257	Intermediate Similarity	NPC168829
0.8254	Intermediate Similarity	NPC138472
0.8254	Intermediate Similarity	NPC111845
0.8254	Intermediate Similarity	NPC227719
0.8246	Intermediate Similarity	NPC228425
0.8241	Intermediate Similarity	NPC223393
0.8235	Intermediate Similarity	NPC32322
0.8235	Intermediate Similarity	NPC241001
0.8235	Intermediate Similarity	NPC259703
0.823	Intermediate Similarity	NPC174096
0.823	Intermediate Similarity	NPC226401
0.823	Intermediate Similarity	NPC147634
0.823	Intermediate Similarity	NPC79793
0.823	Intermediate Similarity	NPC120982
0.823	Intermediate Similarity	NPC296683
0.8211	Intermediate Similarity	NPC471077
0.8208	Intermediate Similarity	NPC144682
0.8208	Intermediate Similarity	NPC107522
0.8208	Intermediate Similarity	NPC8392
0.8205	Intermediate Similarity	NPC278652
0.8205	Intermediate Similarity	NPC299180
0.8198	Intermediate Similarity	NPC271274
0.8198	Intermediate Similarity	NPC54765
0.8197	Intermediate Similarity	NPC266705
0.8197	Intermediate Similarity	NPC29008
0.8197	Intermediate Similarity	NPC9067
0.8197	Intermediate Similarity	NPC228771
0.819	Intermediate Similarity	NPC474486
0.8189	Intermediate Similarity	NPC293454
0.8182	Intermediate Similarity	NPC475225
0.8182	Intermediate Similarity	NPC288411
0.8175	Intermediate Similarity	NPC228843
0.8174	Intermediate Similarity	NPC322239
0.8174	Intermediate Similarity	NPC117846
0.8167	Intermediate Similarity	NPC162935
0.8167	Intermediate Similarity	NPC154696
0.8167	Intermediate Similarity	NPC249340
0.8165	Intermediate Similarity	NPC110764
0.8158	Intermediate Similarity	NPC77772
0.8158	Intermediate Similarity	NPC470770
0.8158	Intermediate Similarity	NPC266937
0.8158	Intermediate Similarity	NPC187583
0.8158	Intermediate Similarity	NPC179002
0.8158	Intermediate Similarity	NPC257430
0.8158	Intermediate Similarity	NPC322753
0.8151	Intermediate Similarity	NPC472071
0.8148	Intermediate Similarity	NPC33675
0.8148	Intermediate Similarity	NPC299762
0.8148	Intermediate Similarity	NPC122005
0.8148	Intermediate Similarity	NPC252821
0.8136	Intermediate Similarity	NPC469609
0.813	Intermediate Similarity	NPC470724
0.8125	Intermediate Similarity	NPC320439
0.8125	Intermediate Similarity	NPC153088
0.8113	Intermediate Similarity	NPC245187
0.8108	Intermediate Similarity	NPC219286
0.8108	Intermediate Similarity	NPC99557
0.8103	Intermediate Similarity	NPC249270
0.8099	Intermediate Similarity	NPC121168
0.8099	Intermediate Similarity	NPC297057
0.8099	Intermediate Similarity	NPC30462
0.8099	Intermediate Similarity	NPC11250
0.8095	Intermediate Similarity	NPC243305
0.8091	Intermediate Similarity	NPC269212
0.8091	Intermediate Similarity	NPC235762
0.8091	Intermediate Similarity	NPC471228
0.8087	Intermediate Similarity	NPC62867
0.8087	Intermediate Similarity	NPC302371
0.8087	Intermediate Similarity	NPC177962
0.8083	Intermediate Similarity	NPC129176
0.8077	Intermediate Similarity	NPC70436
0.8073	Intermediate Similarity	NPC225506
0.807	Intermediate Similarity	NPC44732
0.8067	Intermediate Similarity	NPC310338
0.8067	Intermediate Similarity	NPC281298
0.8062	Intermediate Similarity	NPC68292
0.8056	Intermediate Similarity	NPC32674
0.8056	Intermediate Similarity	NPC156313
0.8053	Intermediate Similarity	NPC95344
0.8037	Intermediate Similarity	NPC222146
0.8037	Intermediate Similarity	NPC274678
0.8034	Intermediate Similarity	NPC84999
0.8034	Intermediate Similarity	NPC246760
0.8033	Intermediate Similarity	NPC471187
0.8018	Intermediate Similarity	NPC475580
0.8018	Intermediate Similarity	NPC12278
0.8	Intermediate Similarity	NPC308689
0.8	Intermediate Similarity	NPC225679
0.8	Intermediate Similarity	NPC51015
0.8	Intermediate Similarity	NPC260832
0.8	Intermediate Similarity	NPC165133
0.8	Intermediate Similarity	NPC4493
0.8	Intermediate Similarity	NPC242885
0.8	Intermediate Similarity	NPC135467
0.8	Intermediate Similarity	NPC224527
0.8	Intermediate Similarity	NPC227217
0.8	Intermediate Similarity	NPC12221
0.8	Intermediate Similarity	NPC117780
0.8	Intermediate Similarity	NPC268032
0.8	Intermediate Similarity	NPC56214
0.8	Intermediate Similarity	NPC476632
0.8	Intermediate Similarity	NPC307050
0.8	Intermediate Similarity	NPC297657
0.8	Intermediate Similarity	NPC232316
0.8	Intermediate Similarity	NPC477685
0.8	Intermediate Similarity	NPC277458
0.8	Intermediate Similarity	NPC252105

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 NPC471179 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	1043
0.2-0.3	1500
0.3-0.4	3055
0.4-0.5	1742
0.5-0.6	1060
0.6-0.7	348
0.7-0.8	66
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8807	High Similarity	NPD3021	Approved
0.8807	High Similarity	NPD3022	Approved
0.8571	High Similarity	NPD7635	Approved
0.8302	Intermediate Similarity	NPD288	Approved
0.8288	Intermediate Similarity	NPD2342	Discontinued
0.8208	Intermediate Similarity	NPD844	Approved
0.8208	Intermediate Similarity	NPD1809	Phase 2
0.819	Intermediate Similarity	NPD845	Approved
0.8148	Intermediate Similarity	NPD3020	Approved
0.7982	Intermediate Similarity	NPD4750	Phase 3
0.787	Intermediate Similarity	NPD2859	Approved
0.787	Intermediate Similarity	NPD2860	Approved
0.7869	Intermediate Similarity	NPD3092	Approved
0.7833	Intermediate Similarity	NPD3091	Approved
0.7778	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2933	Approved
0.7778	Intermediate Similarity	NPD2934	Approved
0.7752	Intermediate Similarity	NPD3620	Phase 2
0.7752	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD4059	Approved
0.7705	Intermediate Similarity	NPD3019	Approved
0.7705	Intermediate Similarity	NPD2932	Approved
0.7692	Intermediate Similarity	NPD228	Approved
0.7667	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3094	Phase 2
0.7561	Intermediate Similarity	NPD2286	Discontinued
0.7561	Intermediate Similarity	NPD4626	Approved
0.7561	Intermediate Similarity	NPD1751	Approved
0.7536	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD940	Approved
0.7522	Intermediate Similarity	NPD846	Approved
0.7521	Intermediate Similarity	NPD1792	Phase 2
0.75	Intermediate Similarity	NPD497	Approved
0.7481	Intermediate Similarity	NPD4060	Phase 1
0.748	Intermediate Similarity	NPD4093	Discontinued
0.7479	Intermediate Similarity	NPD9377	Approved
0.7479	Intermediate Similarity	NPD9379	Approved
0.7462	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3095	Discontinued
0.7417	Intermediate Similarity	NPD5283	Phase 1
0.7417	Intermediate Similarity	NPD495	Approved
0.7417	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1398	Phase 1
0.7417	Intermediate Similarity	NPD496	Approved
0.7417	Intermediate Similarity	NPD498	Approved
0.7395	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7340	Approved
0.7338	Intermediate Similarity	NPD2420	Approved
0.7338	Intermediate Similarity	NPD2421	Approved
0.7304	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD1242	Phase 1
0.7273	Intermediate Similarity	NPD2228	Approved
0.7273	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2229	Approved
0.7273	Intermediate Similarity	NPD2234	Approved
0.7266	Intermediate Similarity	NPD1283	Approved
0.7265	Intermediate Similarity	NPD1445	Approved
0.7265	Intermediate Similarity	NPD1444	Approved
0.7264	Intermediate Similarity	NPD111	Approved
0.7258	Intermediate Similarity	NPD5303	Approved
0.7258	Intermediate Similarity	NPD5304	Approved
0.7252	Intermediate Similarity	NPD4625	Phase 3
0.7239	Intermediate Similarity	NPD4097	Suspended
0.7231	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5736	Approved
0.7209	Intermediate Similarity	NPD3055	Approved
0.7209	Intermediate Similarity	NPD3053	Approved
0.7206	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5691	Approved
0.72	Intermediate Similarity	NPD1651	Approved
0.7176	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6674	Discontinued
0.7167	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1201	Approved
0.7154	Intermediate Similarity	NPD2195	Approved
0.7154	Intermediate Similarity	NPD2194	Approved
0.7153	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4589	Approved
0.7132	Intermediate Similarity	NPD6696	Suspended
0.7132	Intermediate Similarity	NPD5310	Approved
0.7132	Intermediate Similarity	NPD5311	Approved
0.7122	Intermediate Similarity	NPD8166	Discontinued
0.7121	Intermediate Similarity	NPD3027	Phase 3
0.712	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3635	Approved
0.7099	Intermediate Similarity	NPD3636	Approved
0.7099	Intermediate Similarity	NPD3637	Approved
0.7087	Intermediate Similarity	NPD3026	Approved
0.7087	Intermediate Similarity	NPD3023	Approved
0.7063	Intermediate Similarity	NPD3024	Approved
0.7063	Intermediate Similarity	NPD3025	Approved
0.7054	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4749	Approved
0.7045	Intermediate Similarity	NPD2606	Approved
0.7045	Intermediate Similarity	NPD2605	Approved
0.7042	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3645	Discontinued
0.7031	Intermediate Similarity	NPD1281	Approved
0.7023	Intermediate Similarity	NPD4624	Approved
0.7023	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6671	Approved
0.7015	Intermediate Similarity	NPD6663	Approved
0.7009	Intermediate Similarity	NPD9500	Approved
0.7008	Intermediate Similarity	NPD9381	Approved
0.7008	Intermediate Similarity	NPD9384	Approved
0.7007	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5155	Approved
0.6992	Remote Similarity	NPD5156	Approved
0.6984	Remote Similarity	NPD7330	Discontinued
0.6963	Remote Similarity	NPD1613	Approved
0.6963	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD943	Approved
0.6957	Remote Similarity	NPD5405	Approved
0.6957	Remote Similarity	NPD5408	Approved
0.6957	Remote Similarity	NPD5404	Approved
0.6957	Remote Similarity	NPD5406	Approved
0.6947	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1470	Approved
0.6929	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9622	Approved
0.6923	Remote Similarity	NPD1669	Approved
0.6917	Remote Similarity	NPD3594	Approved
0.6917	Remote Similarity	NPD3595	Approved
0.6912	Remote Similarity	NPD5735	Approved
0.6901	Remote Similarity	NPD3845	Phase 1
0.6901	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1611	Approved
0.6894	Remote Similarity	NPD257	Approved
0.6894	Remote Similarity	NPD258	Approved
0.688	Remote Similarity	NPD709	Approved
0.687	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2233	Approved
0.6846	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2232	Approved
0.6846	Remote Similarity	NPD2230	Approved
0.6842	Remote Similarity	NPD2861	Phase 2
0.6838	Remote Similarity	NPD3028	Approved
0.6825	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3143	Discontinued
0.6815	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5327	Phase 3
0.6788	Remote Similarity	NPD3657	Discovery
0.6769	Remote Similarity	NPD1610	Phase 2
0.6769	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD9621	Approved
0.6767	Remote Similarity	NPD9619	Approved
0.6767	Remote Similarity	NPD9620	Approved
0.6763	Remote Similarity	NPD7742	Approved
0.6763	Remote Similarity	NPD7743	Approved
0.6763	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7390	Discontinued
0.6721	Remote Similarity	NPD2684	Approved
0.6718	Remote Similarity	NPD3070	Discontinued
0.6715	Remote Similarity	NPD3059	Approved
0.6715	Remote Similarity	NPD4140	Approved
0.6715	Remote Similarity	NPD3062	Approved
0.6715	Remote Similarity	NPD826	Approved
0.6715	Remote Similarity	NPD3061	Approved
0.6715	Remote Similarity	NPD825	Approved
0.6715	Remote Similarity	NPD1558	Phase 1
0.6693	Remote Similarity	NPD7636	Approved
0.6692	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1164	Approved
0.6691	Remote Similarity	NPD5111	Phase 2
0.6691	Remote Similarity	NPD5110	Phase 2
0.6691	Remote Similarity	NPD601	Approved
0.6691	Remote Similarity	NPD597	Approved
0.6691	Remote Similarity	NPD5109	Approved
0.6691	Remote Similarity	NPD598	Approved
0.6667	Remote Similarity	NPD9608	Approved
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD9610	Approved
0.6667	Remote Similarity	NPD4726	Approved
0.6667	Remote Similarity	NPD3300	Phase 2
0.6667	Remote Similarity	NPD4725	Approved
0.6667	Remote Similarity	NPD1791	Approved
0.6667	Remote Similarity	NPD1793	Approved
0.6667	Remote Similarity	NPD4721	Approved
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD1357	Approved
0.6644	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7003	Approved
0.6642	Remote Similarity	NPD1136	Approved
0.6642	Remote Similarity	NPD1130	Approved
0.6642	Remote Similarity	NPD2674	Phase 3
0.6642	Remote Similarity	NPD1132	Approved
0.6641	Remote Similarity	NPD7644	Approved
0.6641	Remote Similarity	NPD3705	Approved
0.664	Remote Similarity	NPD1138	Approved
0.6621	Remote Similarity	NPD7040	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