NPASS Compound

Structure

CID136342 OpenBabel06191715492D 22 22 0 0 0 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 19 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.17
Volume:	336.539
LogP:	5.772
LogD:	4.816
LogS:	-4.445
# Rotatable Bonds:	7
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	3.352
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.931
MDCK Permeability:	2.463902455929201e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.208
Plasma Protein Binding (PPB):	99.67784118652344%
Volume Distribution (VD):	3.98
Pgp-substrate:	1.0689105987548828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.832
CYP2C19-inhibitor:	0.199
CYP2C19-substrate:	0.552
CYP2C9-inhibitor:	0.454
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.373
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.489
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	3.636
Half-life (T1/2):	0.342

ADMET: Toxicity

hERG Blockers:	0.34
Human Hepatotoxicity (H-HT):	0.47
Drug-inuced Liver Injury (DILI):	0.677
AMES Toxicity:	0.737
Rat Oral Acute Toxicity:	0.783
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.965
Carcinogencity:	0.734
Eye Corrosion:	0.26
Eye Irritation:	0.922
Respiratory Toxicity:	0.883

Download Data

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

Natural Product: NPC136342

Natural Product ID:	NPC136342
*Common Name:**	Dihydroauroglaucin
IUPAC Name:	2-[(1E,3E)-hepta-1,3-dienyl]-3,6-dihydroxy-5-(3-methylbut-2-enyl)benzaldehyde
Synonyms:	Dihydroauroglaucin
Standard InCHIKey:	JXIPKNRBDKQMAN-BLHCBFLLSA-N
Standard InCHI:	InChI=1S/C19H24O3/c1-4-5-6-7-8-9-16-17(13-20)19(22)15(12-18(16)21)11-10-14(2)3/h6-10,12-13,21-22H,4-5,11H2,1-3H3/b7-6+,9-8+
SMILES:	CCC/C=C/C=C/c1c(O)cc(c(c1C=O)O)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813665
PubChem CID:	51340292
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002801] Prenylated hydroquinones

*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
NPO30824	Eurotium repens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667972]

☑ 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
Others	5

Activity Type	# Activity
Individual Protein	5
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[489920]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[489920]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Activity	<	40.0	%	PMID[489920]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Activity	<	40.0	%	PMID[489920]
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Activity	<	40.0	%	PMID[489920]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	20.0	ug.mL-1	PMID[489921]
NPT554	Organism	Candida glabrata	Candida glabrata	IC50	=	2.39	ug.mL-1	PMID[489921]

☑ 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 NPC136342 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	274
0.1-0.2	1521
0.2-0.3	3498
0.3-0.4	11063
0.4-0.5	8739
0.5-0.6	6885
0.6-0.7	8404
0.7-0.8	2003
0.8-0.85	227
0.85-0.9	72
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC295202
1.0	High Similarity	NPC227741
1.0	High Similarity	NPC49647
0.9916	High Similarity	NPC131799
0.944	High Similarity	NPC85342
0.9084	High Similarity	NPC206207
0.904	High Similarity	NPC306765
0.9032	High Similarity	NPC152525
0.9032	High Similarity	NPC68756
0.8917	High Similarity	NPC477453
0.8915	High Similarity	NPC242358
0.8915	High Similarity	NPC110609
0.8915	High Similarity	NPC246693
0.8881	High Similarity	NPC187843
0.888	High Similarity	NPC74507
0.888	High Similarity	NPC234890
0.8871	High Similarity	NPC307174
0.8843	High Similarity	NPC269414
0.8828	High Similarity	NPC474546
0.8819	High Similarity	NPC471530
0.8815	High Similarity	NPC329493
0.877	High Similarity	NPC41567
0.875	High Similarity	NPC48248
0.875	High Similarity	NPC163154
0.8722	High Similarity	NPC305060
0.8692	High Similarity	NPC41847
0.8692	High Similarity	NPC205992
0.8682	High Similarity	NPC278928
0.8678	High Similarity	NPC240163
0.8678	High Similarity	NPC161304
0.8651	High Similarity	NPC275145
0.8647	High Similarity	NPC272268
0.8629	High Similarity	NPC7151
0.8629	High Similarity	NPC473662
0.8629	High Similarity	NPC206778
0.8629	High Similarity	NPC216297
0.8629	High Similarity	NPC285829
0.8615	High Similarity	NPC31539
0.8615	High Similarity	NPC199253
0.8615	High Similarity	NPC136588
0.8615	High Similarity	NPC62219
0.8605	High Similarity	NPC3009
0.8594	High Similarity	NPC96915
0.8583	High Similarity	NPC173978
0.8583	High Similarity	NPC142956
0.8582	High Similarity	NPC245923
0.8571	High Similarity	NPC22222
0.8571	High Similarity	NPC281513
0.856	High Similarity	NPC222876
0.856	High Similarity	NPC301987
0.856	High Similarity	NPC179092
0.856	High Similarity	NPC35856
0.856	High Similarity	NPC178395
0.856	High Similarity	NPC26433
0.856	High Similarity	NPC244994
0.856	High Similarity	NPC272454
0.856	High Similarity	NPC115188
0.856	High Similarity	NPC292665
0.856	High Similarity	NPC159760
0.8548	High Similarity	NPC233165
0.8548	High Similarity	NPC184579
0.8538	High Similarity	NPC34414
0.8538	High Similarity	NPC146647
0.8519	High Similarity	NPC141368
0.8516	High Similarity	NPC240744
0.8516	High Similarity	NPC167055
0.8507	High Similarity	NPC474813
0.8507	High Similarity	NPC472308
0.8507	High Similarity	NPC155211
0.8504	High Similarity	NPC477153
0.8485	Intermediate Similarity	NPC70622
0.8473	Intermediate Similarity	NPC198305
0.8473	Intermediate Similarity	NPC55949
0.8462	Intermediate Similarity	NPC282923
0.8456	Intermediate Similarity	NPC216312
0.8456	Intermediate Similarity	NPC29771
0.8456	Intermediate Similarity	NPC471602
0.8456	Intermediate Similarity	NPC256463
0.8456	Intermediate Similarity	NPC111422
0.8456	Intermediate Similarity	NPC306835
0.8456	Intermediate Similarity	NPC476477
0.8456	Intermediate Similarity	NPC299405
0.8456	Intermediate Similarity	NPC162939
0.845	Intermediate Similarity	NPC1991
0.845	Intermediate Similarity	NPC472047
0.845	Intermediate Similarity	NPC160499
0.8438	Intermediate Similarity	NPC4012
0.8438	Intermediate Similarity	NPC310540
0.8425	Intermediate Similarity	NPC300274
0.8421	Intermediate Similarity	NPC115458
0.8421	Intermediate Similarity	NPC52407
0.8421	Intermediate Similarity	NPC314048
0.8413	Intermediate Similarity	NPC472046
0.8409	Intermediate Similarity	NPC7012
0.84	Intermediate Similarity	NPC232178
0.8394	Intermediate Similarity	NPC220496
0.8394	Intermediate Similarity	NPC42262
0.8394	Intermediate Similarity	NPC241349
0.8394	Intermediate Similarity	NPC37992
0.8394	Intermediate Similarity	NPC327916
0.8394	Intermediate Similarity	NPC147542
0.8394	Intermediate Similarity	NPC32749
0.8387	Intermediate Similarity	NPC125252
0.8387	Intermediate Similarity	NPC160199
0.837	Intermediate Similarity	NPC86524
0.8359	Intermediate Similarity	NPC375356
0.8358	Intermediate Similarity	NPC474519
0.8346	Intermediate Similarity	NPC58685
0.8333	Intermediate Similarity	NPC31799
0.8333	Intermediate Similarity	NPC471444
0.8333	Intermediate Similarity	NPC257003
0.8333	Intermediate Similarity	NPC98392
0.8333	Intermediate Similarity	NPC124365
0.8333	Intermediate Similarity	NPC294964
0.8321	Intermediate Similarity	NPC237225
0.832	Intermediate Similarity	NPC184527
0.8308	Intermediate Similarity	NPC3224
0.8308	Intermediate Similarity	NPC231774
0.8306	Intermediate Similarity	NPC108288
0.8296	Intermediate Similarity	NPC278375
0.8296	Intermediate Similarity	NPC283088
0.8295	Intermediate Similarity	NPC199273
0.8295	Intermediate Similarity	NPC236189
0.8295	Intermediate Similarity	NPC117794
0.8284	Intermediate Similarity	NPC477139
0.8284	Intermediate Similarity	NPC53896
0.8284	Intermediate Similarity	NPC225051
0.8281	Intermediate Similarity	NPC244351
0.8281	Intermediate Similarity	NPC282577
0.8281	Intermediate Similarity	NPC11250
0.8279	Intermediate Similarity	NPC302371
0.8273	Intermediate Similarity	NPC474300
0.8271	Intermediate Similarity	NPC244699
0.8271	Intermediate Similarity	NPC471851
0.8271	Intermediate Similarity	NPC474517
0.8271	Intermediate Similarity	NPC72669
0.8268	Intermediate Similarity	NPC165197
0.8268	Intermediate Similarity	NPC190971
0.8261	Intermediate Similarity	NPC183345
0.8258	Intermediate Similarity	NPC99731
0.825	Intermediate Similarity	NPC279887
0.825	Intermediate Similarity	NPC68260
0.8231	Intermediate Similarity	NPC472592
0.8231	Intermediate Similarity	NPC103540
0.8231	Intermediate Similarity	NPC137750
0.8231	Intermediate Similarity	NPC287473
0.8222	Intermediate Similarity	NPC50924
0.8222	Intermediate Similarity	NPC202225
0.8222	Intermediate Similarity	NPC474394
0.8222	Intermediate Similarity	NPC161964
0.8222	Intermediate Similarity	NPC287604
0.8222	Intermediate Similarity	NPC274876
0.8222	Intermediate Similarity	NPC472262
0.8214	Intermediate Similarity	NPC476473
0.8211	Intermediate Similarity	NPC296144
0.8211	Intermediate Similarity	NPC28784
0.8209	Intermediate Similarity	NPC309430
0.8209	Intermediate Similarity	NPC477406
0.8203	Intermediate Similarity	NPC25168
0.8203	Intermediate Similarity	NPC253627
0.8203	Intermediate Similarity	NPC295034
0.8201	Intermediate Similarity	NPC149780
0.8195	Intermediate Similarity	NPC108129
0.8195	Intermediate Similarity	NPC475741
0.8182	Intermediate Similarity	NPC96024
0.8182	Intermediate Similarity	NPC282855
0.8182	Intermediate Similarity	NPC26013
0.8169	Intermediate Similarity	NPC476535
0.8169	Intermediate Similarity	NPC300540
0.8168	Intermediate Similarity	NPC254492
0.8168	Intermediate Similarity	NPC71610
0.8168	Intermediate Similarity	NPC51037
0.8167	Intermediate Similarity	NPC303264
0.8162	Intermediate Similarity	NPC80035
0.8162	Intermediate Similarity	NPC161632
0.8156	Intermediate Similarity	NPC89664
0.8156	Intermediate Similarity	NPC477409
0.8156	Intermediate Similarity	NPC274085
0.8156	Intermediate Similarity	NPC10764
0.8151	Intermediate Similarity	NPC290927
0.8148	Intermediate Similarity	NPC180261
0.8148	Intermediate Similarity	NPC37299
0.8145	Intermediate Similarity	NPC474050
0.8145	Intermediate Similarity	NPC474114
0.8145	Intermediate Similarity	NPC473931
0.8143	Intermediate Similarity	NPC474961
0.814	Intermediate Similarity	NPC297193
0.8134	Intermediate Similarity	NPC17083
0.8129	Intermediate Similarity	NPC315578
0.8125	Intermediate Similarity	NPC216216
0.812	Intermediate Similarity	NPC276238
0.8115	Intermediate Similarity	NPC208229
0.8115	Intermediate Similarity	NPC471535
0.811	Intermediate Similarity	NPC473767
0.8106	Intermediate Similarity	NPC69424
0.8106	Intermediate Similarity	NPC84672
0.8106	Intermediate Similarity	NPC470841
0.8106	Intermediate Similarity	NPC72667
0.8106	Intermediate Similarity	NPC78364
0.8106	Intermediate Similarity	NPC176130

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 NPC136342 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	995
0.2-0.3	1457
0.3-0.4	2760
0.4-0.5	2048
0.5-0.6	1156
0.6-0.7	406
0.7-0.8	47
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8346	Intermediate Similarity	NPD1201	Approved
0.8306	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1470	Approved
0.8099	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD2935	Discontinued
0.7842	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7635	Approved
0.7786	Intermediate Similarity	NPD5406	Approved
0.7786	Intermediate Similarity	NPD5404	Approved
0.7786	Intermediate Similarity	NPD5408	Approved
0.7786	Intermediate Similarity	NPD5405	Approved
0.773	Intermediate Similarity	NPD2346	Discontinued
0.7655	Intermediate Similarity	NPD7390	Discontinued
0.7603	Intermediate Similarity	NPD2532	Approved
0.7603	Intermediate Similarity	NPD2534	Approved
0.7603	Intermediate Similarity	NPD2533	Approved
0.7597	Intermediate Similarity	NPD9493	Approved
0.7586	Intermediate Similarity	NPD3300	Phase 2
0.7557	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1164	Approved
0.7521	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD9266	Approved
0.752	Intermediate Similarity	NPD74	Approved
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD2932	Approved
0.7479	Intermediate Similarity	NPD844	Approved
0.744	Intermediate Similarity	NPD9267	Approved
0.744	Intermediate Similarity	NPD9264	Approved
0.744	Intermediate Similarity	NPD9263	Approved
0.7417	Intermediate Similarity	NPD288	Approved
0.74	Intermediate Similarity	NPD3226	Approved
0.7343	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5951	Approved
0.7302	Intermediate Similarity	NPD2342	Discontinued
0.7293	Intermediate Similarity	NPD5691	Approved
0.7246	Intermediate Similarity	NPD2798	Approved
0.7226	Intermediate Similarity	NPD1283	Approved
0.7222	Intermediate Similarity	NPD2799	Discontinued
0.7215	Intermediate Similarity	NPD6232	Discontinued
0.7211	Intermediate Similarity	NPD7003	Approved
0.7183	Intermediate Similarity	NPD943	Approved
0.7167	Intermediate Similarity	NPD845	Approved
0.7164	Intermediate Similarity	NPD1651	Approved
0.7163	Intermediate Similarity	NPD2313	Discontinued
0.7123	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD9261	Approved
0.7113	Intermediate Similarity	NPD6663	Approved
0.7103	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1607	Approved
0.7081	Intermediate Similarity	NPD7473	Discontinued
0.7075	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD9494	Approved
0.7071	Intermediate Similarity	NPD5736	Approved
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7054	Intermediate Similarity	NPD4750	Phase 3
0.7045	Intermediate Similarity	NPD497	Approved
0.7045	Intermediate Similarity	NPD9281	Approved
0.7044	Intermediate Similarity	NPD6959	Discontinued
0.7042	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD411	Approved
0.702	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD447	Suspended
0.7007	Intermediate Similarity	NPD2344	Approved
0.7007	Intermediate Similarity	NPD1281	Approved
0.7	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7819	Suspended
0.6987	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6696	Suspended
0.6977	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.697	Remote Similarity	NPD496	Approved
0.697	Remote Similarity	NPD495	Approved
0.697	Remote Similarity	NPD498	Approved
0.6963	Remote Similarity	NPD9545	Approved
0.6963	Remote Similarity	NPD3091	Approved
0.6957	Remote Similarity	NPD9717	Approved
0.6944	Remote Similarity	NPD2979	Phase 3
0.6944	Remote Similarity	NPD1240	Approved
0.6934	Remote Similarity	NPD3026	Approved
0.6934	Remote Similarity	NPD3496	Discontinued
0.6934	Remote Similarity	NPD3023	Approved
0.6923	Remote Similarity	NPD3764	Approved
0.6912	Remote Similarity	NPD3025	Approved
0.6912	Remote Similarity	NPD3024	Approved
0.6911	Remote Similarity	NPD1809	Phase 2
0.6899	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5711	Approved
0.6894	Remote Similarity	NPD5710	Approved
0.6884	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.688	Remote Similarity	NPD3020	Approved
0.6879	Remote Similarity	NPD2801	Approved
0.6871	Remote Similarity	NPD1510	Phase 2
0.687	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6671	Approved
0.6864	Remote Similarity	NPD8150	Discontinued
0.6853	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7008	Discontinued
0.6846	Remote Similarity	NPD2182	Approved
0.6842	Remote Similarity	NPD1398	Phase 1
0.6835	Remote Similarity	NPD3972	Approved
0.6829	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4955	Approved
0.6826	Remote Similarity	NPD5026	Approved
0.6826	Remote Similarity	NPD4954	Approved
0.6826	Remote Similarity	NPD5034	Approved
0.6826	Remote Similarity	NPD5028	Approved
0.6826	Remote Similarity	NPD36	Approved
0.6821	Remote Similarity	NPD2309	Approved
0.6815	Remote Similarity	NPD7340	Approved
0.6815	Remote Similarity	NPD6844	Discontinued
0.6809	Remote Similarity	NPD1203	Approved
0.6802	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1237	Approved
0.6795	Remote Similarity	NPD4380	Phase 2
0.6788	Remote Similarity	NPD5844	Phase 1
0.6786	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8313	Approved
0.6786	Remote Similarity	NPD8312	Approved
0.6786	Remote Similarity	NPD1755	Approved
0.6783	Remote Similarity	NPD6832	Phase 2
0.6781	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2860	Approved
0.6774	Remote Similarity	NPD2859	Approved
0.6766	Remote Similarity	NPD6559	Discontinued
0.6766	Remote Similarity	NPD5030	Phase 2
0.6763	Remote Similarity	NPD3092	Approved
0.6763	Remote Similarity	NPD1611	Approved
0.6759	Remote Similarity	NPD520	Approved
0.6755	Remote Similarity	NPD8166	Discontinued
0.6753	Remote Similarity	NPD6273	Approved
0.6741	Remote Similarity	NPD3317	Approved
0.6739	Remote Similarity	NPD1778	Approved
0.6738	Remote Similarity	NPD1876	Approved
0.6731	Remote Similarity	NPD7458	Discontinued
0.673	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1929	Approved
0.6719	Remote Similarity	NPD1930	Approved
0.6713	Remote Similarity	NPD4208	Discontinued
0.6712	Remote Similarity	NPD4060	Phase 1
0.6711	Remote Similarity	NPD4476	Approved
0.6711	Remote Similarity	NPD4477	Approved
0.6709	Remote Similarity	NPD1934	Approved
0.6694	Remote Similarity	NPD2934	Approved
0.6694	Remote Similarity	NPD2933	Approved
0.6692	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2797	Approved
0.669	Remote Similarity	NPD3094	Phase 2
0.6689	Remote Similarity	NPD2800	Approved
0.6689	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD5029	Approved
0.6667	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5027	Approved
0.6667	Remote Similarity	NPD5031	Approved
0.6667	Remote Similarity	NPD3021	Approved
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD164	Approved
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5038	Approved
0.6667	Remote Similarity	NPD5037	Approved
0.6667	Remote Similarity	NPD6213	Phase 3
0.6667	Remote Similarity	NPD3022	Approved
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3400	Discontinued
0.6645	Remote Similarity	NPD4628	Phase 3
0.6644	Remote Similarity	NPD4308	Phase 3
0.6643	Remote Similarity	NPD1019	Discontinued
0.6641	Remote Similarity	NPD846	Approved
0.6641	Remote Similarity	NPD940	Approved
0.6629	Remote Similarity	NPD6535	Approved
0.6629	Remote Similarity	NPD6534	Approved
0.6625	Remote Similarity	NPD5402	Approved
0.6625	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1549	Phase 2
0.6621	Remote Similarity	NPD4625	Phase 3
0.6619	Remote Similarity	NPD3095	Discontinued
0.6619	Remote Similarity	NPD2286	Discontinued
0.6619	Remote Similarity	NPD4059	Approved
0.6614	Remote Similarity	NPD2066	Phase 3
0.6608	Remote Similarity	NPD5036	Approved
0.6601	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6100	Approved
0.66	Remote Similarity	NPD2531	Phase 2
0.66	Remote Similarity	NPD2438	Suspended
0.66	Remote Similarity	NPD6099	Approved
0.66	Remote Similarity	NPD2796	Approved
0.6596	Remote Similarity	NPD4878	Approved
0.6596	Remote Similarity	NPD9269	Phase 2
0.6593	Remote Similarity	NPD7159	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