NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.13
Volume:	255.281
LogP:	4.161
LogD:	3.773
LogS:	-3.485
# 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:	0.777
Synthetic Accessibility Score:	2.469
Fsp3:	0.333
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:	-4.88
MDCK Permeability:	1.7365544408676215e-05
Pgp-inhibitor:	0.154
Pgp-substrate:	0.096
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.314
Plasma Protein Binding (PPB):	97.7828598022461%
Volume Distribution (VD):	1.149
Pgp-substrate:	1.1450917720794678%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.459
CYP2C19-substrate:	0.263
CYP2C9-inhibitor:	0.505
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.85
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.37
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	10.673
Half-life (T1/2):	0.49

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.728
AMES Toxicity:	0.504
Rat Oral Acute Toxicity:	0.432
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.936
Carcinogencity:	0.294
Eye Corrosion:	0.085
Eye Irritation:	0.971
Respiratory Toxicity:	0.88

Download Data

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

Natural Product: NPC151537

Natural Product ID:	NPC151537
*Common Name:**	2,7-Dihydroxycadalene
IUPAC Name:	1,6-dimethyl-4-propan-2-ylnaphthalene-2,7-diol
Synonyms:
Standard InCHIKey:	OKOXDXHTJZNGOM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H18O2/c1-8(2)11-6-15(17)10(4)12-7-14(16)9(3)5-13(11)12/h5-8,16-17H,1-4H3
SMILES:	CC(C)c1cc(c(C)c2cc(c(C)cc12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386325
PubChem CID:	157057
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	2

Activity Type	# Activity
Organism	1
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	3800.0	nM	PMID[536108]
NPT3494	Organism	Coxsackievirus	Coxsackievirus	IC50	=	10100.0	nM	PMID[536108]

☑ 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 NPC151537 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	332
0.1-0.2	1925
0.2-0.3	4545
0.3-0.4	12850
0.4-0.5	6406
0.5-0.6	8285
0.6-0.7	6334
0.7-0.8	1670
0.8-0.85	244
0.85-0.9	91
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC58865
0.9423	High Similarity	NPC151477
0.9346	High Similarity	NPC46940
0.9327	High Similarity	NPC21594
0.9259	High Similarity	NPC715
0.9252	High Similarity	NPC95716
0.9231	High Similarity	NPC117115
0.9174	High Similarity	NPC195922
0.9135	High Similarity	NPC238696
0.9099	High Similarity	NPC304510
0.9099	High Similarity	NPC172219
0.9074	High Similarity	NPC260323
0.9074	High Similarity	NPC176279
0.9065	High Similarity	NPC314187
0.9018	High Similarity	NPC471671
0.9	High Similarity	NPC249270
0.9	High Similarity	NPC107240
0.8991	High Similarity	NPC250323
0.8991	High Similarity	NPC471179
0.8981	High Similarity	NPC132720
0.8981	High Similarity	NPC224870
0.8972	High Similarity	NPC95344
0.8972	High Similarity	NPC11554
0.8938	High Similarity	NPC176893
0.8938	High Similarity	NPC469644
0.8919	High Similarity	NPC192948
0.8919	High Similarity	NPC35797
0.8909	High Similarity	NPC263753
0.8909	High Similarity	NPC117846
0.8899	High Similarity	NPC469912
0.8868	High Similarity	NPC138942
0.8857	High Similarity	NPC168829
0.885	High Similarity	NPC154030
0.8839	High Similarity	NPC38893
0.8839	High Similarity	NPC477137
0.8839	High Similarity	NPC471668
0.8839	High Similarity	NPC115808
0.8839	High Similarity	NPC308311
0.8807	High Similarity	NPC141782
0.8807	High Similarity	NPC13482
0.8807	High Similarity	NPC296683
0.8793	High Similarity	NPC71094
0.8785	High Similarity	NPC54765
0.8774	High Similarity	NPC272029
0.8774	High Similarity	NPC288411
0.8772	High Similarity	NPC151197
0.8761	High Similarity	NPC477136
0.8761	High Similarity	NPC470760
0.8761	High Similarity	NPC299180
0.875	High Similarity	NPC246760
0.875	High Similarity	NPC84999
0.8739	High Similarity	NPC322239
0.8727	High Similarity	NPC165770
0.8727	High Similarity	NPC224527
0.8727	High Similarity	NPC225679
0.8727	High Similarity	NPC4493
0.8727	High Similarity	NPC476632
0.8716	High Similarity	NPC202647
0.8692	High Similarity	NPC99557
0.8692	High Similarity	NPC219286
0.8684	High Similarity	NPC469609
0.8673	High Similarity	NPC219112
0.8667	High Similarity	NPC72729
0.8667	High Similarity	NPC211885
0.8661	High Similarity	NPC268160
0.8654	High Similarity	NPC32674
0.8654	High Similarity	NPC77492
0.8654	High Similarity	NPC79241
0.8654	High Similarity	NPC156313
0.8654	High Similarity	NPC6597
0.8649	High Similarity	NPC166995
0.8649	High Similarity	NPC43525
0.8644	High Similarity	NPC224342
0.8632	High Similarity	NPC297057
0.8624	High Similarity	NPC174981
0.8611	High Similarity	NPC271274
0.8609	High Similarity	NPC93071
0.8609	High Similarity	NPC126002
0.8584	High Similarity	NPC147179
0.8571	High Similarity	NPC23804
0.8571	High Similarity	NPC317869
0.8558	High Similarity	NPC312132
0.8558	High Similarity	NPC259512
0.8547	High Similarity	NPC39029
0.8545	High Similarity	NPC19808
0.8545	High Similarity	NPC299568
0.8545	High Similarity	NPC186385
0.8545	High Similarity	NPC33728
0.8534	High Similarity	NPC478121
0.8522	High Similarity	NPC328694
0.8522	High Similarity	NPC206
0.8509	High Similarity	NPC92
0.8509	High Similarity	NPC469663
0.8509	High Similarity	NPC141001
0.8509	High Similarity	NPC308828
0.8505	High Similarity	NPC233827
0.8505	High Similarity	NPC168393
0.8496	Intermediate Similarity	NPC12656
0.8496	Intermediate Similarity	NPC471534
0.8482	Intermediate Similarity	NPC228425
0.8482	Intermediate Similarity	NPC473521
0.8475	Intermediate Similarity	NPC176208
0.8462	Intermediate Similarity	NPC274678
0.8462	Intermediate Similarity	NPC241001
0.8462	Intermediate Similarity	NPC32322
0.8462	Intermediate Similarity	NPC129176
0.8462	Intermediate Similarity	NPC8392
0.8462	Intermediate Similarity	NPC259703
0.8455	Intermediate Similarity	NPC63698
0.8455	Intermediate Similarity	NPC233835
0.8455	Intermediate Similarity	NPC262365
0.8455	Intermediate Similarity	NPC61885
0.8448	Intermediate Similarity	NPC191866
0.844	Intermediate Similarity	NPC469913
0.844	Intermediate Similarity	NPC248904
0.8435	Intermediate Similarity	NPC16030
0.8426	Intermediate Similarity	NPC244513
0.8426	Intermediate Similarity	NPC327811
0.8426	Intermediate Similarity	NPC475225
0.8426	Intermediate Similarity	NPC254965
0.8426	Intermediate Similarity	NPC227458
0.8426	Intermediate Similarity	NPC218879
0.8421	Intermediate Similarity	NPC469719
0.8417	Intermediate Similarity	NPC124030
0.8417	Intermediate Similarity	NPC105031
0.8411	Intermediate Similarity	NPC12221
0.8407	Intermediate Similarity	NPC321589
0.8396	Intermediate Similarity	NPC122005
0.8396	Intermediate Similarity	NPC252821
0.8396	Intermediate Similarity	NPC299762
0.8396	Intermediate Similarity	NPC92730
0.8396	Intermediate Similarity	NPC33675
0.8393	Intermediate Similarity	NPC470770
0.8393	Intermediate Similarity	NPC266937
0.8393	Intermediate Similarity	NPC322753
0.8393	Intermediate Similarity	NPC77772
0.839	Intermediate Similarity	NPC154696
0.839	Intermediate Similarity	NPC237667
0.839	Intermediate Similarity	NPC162935
0.839	Intermediate Similarity	NPC249340
0.8381	Intermediate Similarity	NPC292730
0.8381	Intermediate Similarity	NPC82664
0.8381	Intermediate Similarity	NPC216520
0.8381	Intermediate Similarity	NPC132271
0.8381	Intermediate Similarity	NPC473388
0.8376	Intermediate Similarity	NPC475245
0.8376	Intermediate Similarity	NPC103916
0.8365	Intermediate Similarity	NPC245187
0.8365	Intermediate Similarity	NPC128062
0.8364	Intermediate Similarity	NPC320439
0.8362	Intermediate Similarity	NPC63010
0.8349	Intermediate Similarity	NPC37802
0.8348	Intermediate Similarity	NPC261973
0.8347	Intermediate Similarity	NPC325294
0.8347	Intermediate Similarity	NPC100414
0.8347	Intermediate Similarity	NPC321822
0.8347	Intermediate Similarity	NPC43000
0.8333	Intermediate Similarity	NPC473137
0.8333	Intermediate Similarity	NPC269212
0.8333	Intermediate Similarity	NPC471228
0.8333	Intermediate Similarity	NPC235762
0.8319	Intermediate Similarity	NPC471794
0.8319	Intermediate Similarity	NPC302371
0.8319	Intermediate Similarity	NPC11250
0.8319	Intermediate Similarity	NPC62867
0.8319	Intermediate Similarity	NPC121168
0.8319	Intermediate Similarity	NPC177962
0.8318	Intermediate Similarity	NPC225506
0.8306	Intermediate Similarity	NPC41847
0.8305	Intermediate Similarity	NPC24125
0.8305	Intermediate Similarity	NPC328504
0.8304	Intermediate Similarity	NPC44732
0.8302	Intermediate Similarity	NPC225464
0.8288	Intermediate Similarity	NPC306295
0.8286	Intermediate Similarity	NPC144682
0.8286	Intermediate Similarity	NPC26244
0.8286	Intermediate Similarity	NPC222146
0.8279	Intermediate Similarity	NPC108164
0.8279	Intermediate Similarity	NPC471077
0.8279	Intermediate Similarity	NPC53781
0.8276	Intermediate Similarity	NPC277588
0.8273	Intermediate Similarity	NPC99836
0.8273	Intermediate Similarity	NPC201662
0.8273	Intermediate Similarity	NPC12640
0.8273	Intermediate Similarity	NPC67250
0.8269	Intermediate Similarity	NPC271440
0.8261	Intermediate Similarity	NPC472893
0.8257	Intermediate Similarity	NPC30506
0.8257	Intermediate Similarity	NPC475580
0.8257	Intermediate Similarity	NPC102216
0.8257	Intermediate Similarity	NPC119860
0.825	Intermediate Similarity	NPC53567
0.825	Intermediate Similarity	NPC471187
0.8246	Intermediate Similarity	NPC319803
0.8246	Intermediate Similarity	NPC35344
0.8246	Intermediate Similarity	NPC141003
0.8241	Intermediate Similarity	NPC477685
0.8241	Intermediate Similarity	NPC51015
0.8241	Intermediate Similarity	NPC252105
0.823	Intermediate Similarity	NPC308689

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 NPC151537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	1044
0.2-0.3	1286
0.3-0.4	3018
0.4-0.5	1828
0.5-0.6	1144
0.6-0.7	387
0.7-0.8	80
0.8-0.85	14
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8991	High Similarity	NPD7635	Approved
0.8704	High Similarity	NPD2342	Discontinued
0.8571	High Similarity	NPD3020	Approved
0.8558	High Similarity	NPD288	Approved
0.8545	High Similarity	NPD4750	Phase 3
0.8462	Intermediate Similarity	NPD844	Approved
0.8286	Intermediate Similarity	NPD2859	Approved
0.8286	Intermediate Similarity	NPD1809	Phase 2
0.8286	Intermediate Similarity	NPD2860	Approved
0.8269	Intermediate Similarity	NPD845	Approved
0.8214	Intermediate Similarity	NPD3022	Approved
0.8214	Intermediate Similarity	NPD3021	Approved
0.819	Intermediate Similarity	NPD2934	Approved
0.819	Intermediate Similarity	NPD2933	Approved
0.8099	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD846	Approved
0.8073	Intermediate Similarity	NPD940	Approved
0.8067	Intermediate Similarity	NPD2286	Discontinued
0.8051	Intermediate Similarity	NPD3091	Approved
0.8019	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD497	Approved
0.8	Intermediate Similarity	NPD4625	Phase 3
0.7982	Intermediate Similarity	NPD1242	Phase 1
0.7982	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD3092	Approved
0.7931	Intermediate Similarity	NPD496	Approved
0.7931	Intermediate Similarity	NPD495	Approved
0.7931	Intermediate Similarity	NPD498	Approved
0.7917	Intermediate Similarity	NPD2932	Approved
0.7917	Intermediate Similarity	NPD3019	Approved
0.7917	Intermediate Similarity	NPD4059	Approved
0.7881	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD4093	Discontinued
0.7787	Intermediate Similarity	NPD1201	Approved
0.7769	Intermediate Similarity	NPD4626	Approved
0.7769	Intermediate Similarity	NPD1751	Approved
0.7742	Intermediate Similarity	NPD1283	Approved
0.7739	Intermediate Similarity	NPD1792	Phase 2
0.7686	Intermediate Similarity	NPD1651	Approved
0.768	Intermediate Similarity	NPD3094	Phase 2
0.7679	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD3095	Discontinued
0.7603	Intermediate Similarity	NPD5304	Approved
0.7603	Intermediate Similarity	NPD5303	Approved
0.76	Intermediate Similarity	NPD6696	Suspended
0.7576	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD1470	Approved
0.7538	Intermediate Similarity	NPD4060	Phase 1
0.752	Intermediate Similarity	NPD4749	Approved
0.7519	Intermediate Similarity	NPD5406	Approved
0.7519	Intermediate Similarity	NPD5408	Approved
0.7519	Intermediate Similarity	NPD5404	Approved
0.7519	Intermediate Similarity	NPD5405	Approved
0.75	Intermediate Similarity	NPD111	Approved
0.75	Intermediate Similarity	NPD1281	Approved
0.748	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD4589	Approved
0.7479	Intermediate Similarity	NPD2228	Approved
0.7479	Intermediate Similarity	NPD2234	Approved
0.7479	Intermediate Similarity	NPD1398	Phase 1
0.7479	Intermediate Similarity	NPD2229	Approved
0.7478	Intermediate Similarity	NPD1444	Approved
0.7478	Intermediate Similarity	NPD1445	Approved
0.7458	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7340	Approved
0.7424	Intermediate Similarity	NPD4097	Suspended
0.7422	Intermediate Similarity	NPD2861	Phase 2
0.7422	Intermediate Similarity	NPD5736	Approved
0.7417	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5691	Approved
0.7391	Intermediate Similarity	NPD7390	Discontinued
0.7385	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1669	Approved
0.736	Intermediate Similarity	NPD1611	Approved
0.736	Intermediate Similarity	NPD1610	Phase 2
0.7355	Intermediate Similarity	NPD709	Approved
0.7344	Intermediate Similarity	NPD2195	Approved
0.7344	Intermediate Similarity	NPD2194	Approved
0.7338	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5155	Approved
0.7308	Intermediate Similarity	NPD5156	Approved
0.7287	Intermediate Similarity	NPD3637	Approved
0.7287	Intermediate Similarity	NPD3635	Approved
0.7287	Intermediate Similarity	NPD3636	Approved
0.728	Intermediate Similarity	NPD3026	Approved
0.728	Intermediate Similarity	NPD3023	Approved
0.7258	Intermediate Similarity	NPD3025	Approved
0.7258	Intermediate Similarity	NPD3024	Approved
0.7252	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD2606	Approved
0.7231	Intermediate Similarity	NPD4908	Phase 1
0.7231	Intermediate Similarity	NPD2605	Approved
0.7226	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD9500	Approved
0.7213	Intermediate Similarity	NPD6671	Approved
0.7209	Intermediate Similarity	NPD4624	Approved
0.72	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6663	Approved
0.7193	Intermediate Similarity	NPD3028	Approved
0.719	Intermediate Similarity	NPD5283	Phase 1
0.7177	Intermediate Similarity	NPD7330	Discontinued
0.7143	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1164	Approved
0.7099	Intermediate Similarity	NPD3594	Approved
0.7099	Intermediate Similarity	NPD3595	Approved
0.708	Intermediate Similarity	NPD4725	Approved
0.708	Intermediate Similarity	NPD4726	Approved
0.708	Intermediate Similarity	NPD4721	Approved
0.705	Intermediate Similarity	NPD7003	Approved
0.704	Intermediate Similarity	NPD1548	Phase 1
0.7031	Intermediate Similarity	NPD2230	Approved
0.7031	Intermediate Similarity	NPD2233	Approved
0.7031	Intermediate Similarity	NPD2232	Approved
0.7025	Intermediate Similarity	NPD228	Approved
0.7023	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2420	Approved
0.7021	Intermediate Similarity	NPD2421	Approved
0.7016	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2979	Phase 3
0.7007	Intermediate Similarity	NPD6099	Approved
0.7007	Intermediate Similarity	NPD6100	Approved
0.6992	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5327	Phase 3
0.6977	Remote Similarity	NPD4659	Approved
0.697	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5735	Approved
0.6957	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6405	Approved
0.694	Remote Similarity	NPD6407	Approved
0.6934	Remote Similarity	NPD7742	Approved
0.6934	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7743	Approved
0.6917	Remote Similarity	NPD3027	Phase 3
0.6901	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7041	Phase 2
0.6899	Remote Similarity	NPD1608	Approved
0.6897	Remote Similarity	NPD1616	Discontinued
0.6889	Remote Similarity	NPD2238	Phase 2
0.6889	Remote Similarity	NPD4140	Approved
0.6875	Remote Similarity	NPD1980	Approved
0.6875	Remote Similarity	NPD1981	Approved
0.6875	Remote Similarity	NPD1983	Approved
0.6875	Remote Similarity	NPD3143	Discontinued
0.687	Remote Similarity	NPD1133	Approved
0.687	Remote Similarity	NPD1135	Approved
0.687	Remote Similarity	NPD1129	Approved
0.687	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1131	Approved
0.687	Remote Similarity	NPD1134	Approved
0.687	Remote Similarity	NPD4103	Phase 2
0.6866	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9608	Approved
0.6864	Remote Similarity	NPD9610	Approved
0.686	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1791	Approved
0.6855	Remote Similarity	NPD1793	Approved
0.6835	Remote Similarity	NPD5762	Approved
0.6835	Remote Similarity	NPD5763	Approved
0.6829	Remote Similarity	NPD9377	Approved
0.6829	Remote Similarity	NPD9379	Approved
0.6818	Remote Similarity	NPD6584	Phase 3
0.6812	Remote Similarity	NPD4108	Discontinued
0.6806	Remote Similarity	NPD6090	Discontinued
0.6803	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6387	Discontinued
0.6797	Remote Similarity	NPD2668	Approved
0.6797	Remote Similarity	NPD2667	Approved
0.6788	Remote Similarity	NPD6353	Approved
0.6788	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2157	Approved
0.6786	Remote Similarity	NPD4256	Phase 2
0.6786	Remote Similarity	NPD7037	Approved
0.6786	Remote Similarity	NPD4257	Approved
0.6769	Remote Similarity	NPD2562	Approved
0.6769	Remote Similarity	NPD3070	Discontinued
0.6769	Remote Similarity	NPD2561	Approved
0.6765	Remote Similarity	NPD943	Approved
0.6765	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1613	Approved
0.6763	Remote Similarity	NPD2531	Phase 2
0.6763	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2438	Suspended
0.6763	Remote Similarity	NPD2935	Discontinued
0.675	Remote Similarity	NPD968	Approved
0.6746	Remote Similarity	NPD7636	Approved
0.6744	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3055	Approved
0.6742	Remote Similarity	NPD3053	Approved
0.6741	Remote Similarity	NPD3764	Approved
0.6739	Remote Similarity	NPD3553	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