NPASS Compound

Structure

NPC285622 OpenBabel07101718242D 27 30 0 0 1 0 0 0 0 0999 V2000 -3.3022 2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7035 1.9090 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3559 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3559 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1211 1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1266 1.3090 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 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7089 2.0135 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 -2.4899 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 -1.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 11 14 1 0 0 0 0 12 22 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 12 1 6 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 18 11 1 6 0 0 0 18 19 1 0 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 22 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.21
Volume:	387.388
LogP:	4.585
LogD:	3.694
LogS:	-5.569
# Rotatable Bonds:	4
TPSA:	58.64
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.652
Synthetic Accessibility Score:	4.39
Fsp3:	0.545
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:	-4.683
MDCK Permeability:	3.9864815335022286e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.331
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.244

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	95.5859375%
Volume Distribution (VD):	1.365
Pgp-substrate:	5.618417263031006%

ADMET: Metabolism

CYP1A2-inhibitor:	0.131
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.914
CYP2C19-substrate:	0.718
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.241
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.826
CYP3A4-substrate:	0.543

ADMET: Excretion

Clearance (CL):	8.589
Half-life (T1/2):	0.1

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.927
Drug-inuced Liver Injury (DILI):	0.849
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.552
Maximum Recommended Daily Dose:	0.635
Skin Sensitization:	0.867
Carcinogencity:	0.332
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.351

Download Data

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

Natural Product: NPC285622

Natural Product ID:	NPC285622
*Common Name:**	Mollenine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WLPAAGQHCJNVMM-UBBRYJJRSA-N
Standard InCHI:	InChI=1S/C22H28N2O3/c1-13(2)9-10-22-12-17-20(26)27-18(11-14(3)4)19(25)24(17)21(22)23-16-8-6-5-7-15(16)22/h5-9,14,17-18,21,23H,10-12H2,1-4H3/t17-,18-,21+,22+/m1/s1
SMILES:	CC(=CC[C@@]12C[C@H]3N([C@@H]1Nc1c2cccc1)C(=O)[C@H](OC3=O)CC(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513895
PubChem CID:	5324478
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0000394] Alpha amino acid esters

*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
NPO32796	eupenicillium molle	Species	Aspergillaceae	Eukaryota	ascostromata	n.a.	n.a.	PMID[9644070]

☑ 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
GI50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	31000.0	nM	PMID[451191]

☑ 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 NPC285622 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	228
0.1-0.2	1051
0.2-0.3	4573
0.3-0.4	24724
0.4-0.5	8125
0.5-0.6	3069
0.6-0.7	793
0.7-0.8	130
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8084	Intermediate Similarity	NPC68650
0.8084	Intermediate Similarity	NPC309531
0.8084	Intermediate Similarity	NPC472102
0.8023	Intermediate Similarity	NPC259626
0.8	Intermediate Similarity	NPC279527
0.8	Intermediate Similarity	NPC214960
0.7966	Intermediate Similarity	NPC2933
0.7964	Intermediate Similarity	NPC222029
0.7929	Intermediate Similarity	NPC286871
0.791	Intermediate Similarity	NPC256288
0.7857	Intermediate Similarity	NPC113946
0.7818	Intermediate Similarity	NPC473329
0.7811	Intermediate Similarity	NPC276085
0.7778	Intermediate Similarity	NPC473615
0.7771	Intermediate Similarity	NPC66936
0.7736	Intermediate Similarity	NPC471123
0.7735	Intermediate Similarity	NPC229484
0.7719	Intermediate Similarity	NPC176983
0.7719	Intermediate Similarity	NPC282339
0.7719	Intermediate Similarity	NPC99632
0.7714	Intermediate Similarity	NPC177261
0.7709	Intermediate Similarity	NPC159963
0.7706	Intermediate Similarity	NPC193410
0.7692	Intermediate Similarity	NPC292675
0.7661	Intermediate Similarity	NPC248117
0.765	Intermediate Similarity	NPC473298
0.7647	Intermediate Similarity	NPC61013
0.763	Intermediate Similarity	NPC472106
0.7627	Intermediate Similarity	NPC203202
0.7627	Intermediate Similarity	NPC264482
0.7616	Intermediate Similarity	NPC472101
0.7616	Intermediate Similarity	NPC472120
0.7602	Intermediate Similarity	NPC471122
0.7558	Intermediate Similarity	NPC225319
0.7543	Intermediate Similarity	NPC224970
0.7543	Intermediate Similarity	NPC167724
0.7543	Intermediate Similarity	NPC223595
0.7541	Intermediate Similarity	NPC181928
0.7541	Intermediate Similarity	NPC14994
0.7529	Intermediate Similarity	NPC471124
0.7514	Intermediate Similarity	NPC25401
0.7514	Intermediate Similarity	NPC472117
0.75	Intermediate Similarity	NPC36495
0.7485	Intermediate Similarity	NPC29285
0.7448	Intermediate Similarity	NPC477179
0.7444	Intermediate Similarity	NPC6974
0.7444	Intermediate Similarity	NPC99043
0.7444	Intermediate Similarity	NPC218594
0.7442	Intermediate Similarity	NPC123241
0.7437	Intermediate Similarity	NPC471197
0.7432	Intermediate Similarity	NPC307396
0.7423	Intermediate Similarity	NPC469560
0.7416	Intermediate Similarity	NPC242269
0.7416	Intermediate Similarity	NPC139085
0.7416	Intermediate Similarity	NPC251212
0.7416	Intermediate Similarity	NPC214626
0.7414	Intermediate Similarity	NPC293458
0.7409	Intermediate Similarity	NPC254850
0.7409	Intermediate Similarity	NPC477180
0.7409	Intermediate Similarity	NPC477181
0.7409	Intermediate Similarity	NPC477178
0.7403	Intermediate Similarity	NPC11149
0.74	Intermediate Similarity	NPC471198
0.7389	Intermediate Similarity	NPC186669
0.7385	Intermediate Similarity	NPC285192
0.7385	Intermediate Similarity	NPC471950
0.7385	Intermediate Similarity	NPC471945
0.7371	Intermediate Similarity	NPC477174
0.7371	Intermediate Similarity	NPC477173
0.7371	Intermediate Similarity	NPC470490
0.7368	Intermediate Similarity	NPC478076
0.736	Intermediate Similarity	NPC355
0.7347	Intermediate Similarity	NPC471951
0.7347	Intermediate Similarity	NPC471946
0.7333	Intermediate Similarity	NPC470488
0.7322	Intermediate Similarity	NPC477159
0.7312	Intermediate Similarity	NPC284706
0.7302	Intermediate Similarity	NPC34717
0.7296	Intermediate Similarity	NPC470491
0.7296	Intermediate Similarity	NPC475259
0.7288	Intermediate Similarity	NPC472114
0.7288	Intermediate Similarity	NPC472115
0.7243	Intermediate Similarity	NPC52262
0.7235	Intermediate Similarity	NPC109787
0.7234	Intermediate Similarity	NPC276430
0.7231	Intermediate Similarity	NPC470489
0.7225	Intermediate Similarity	NPC90967
0.7222	Intermediate Similarity	NPC191817
0.7222	Intermediate Similarity	NPC96901
0.7222	Intermediate Similarity	NPC476425
0.7222	Intermediate Similarity	NPC475359
0.7216	Intermediate Similarity	NPC471436
0.7207	Intermediate Similarity	NPC472118
0.7198	Intermediate Similarity	NPC260075
0.7182	Intermediate Similarity	NPC329338
0.7182	Intermediate Similarity	NPC469726
0.7181	Intermediate Similarity	NPC128582
0.7143	Intermediate Similarity	NPC77777
0.712	Intermediate Similarity	NPC221687
0.7118	Intermediate Similarity	NPC264589
0.7114	Intermediate Similarity	NPC54744
0.7097	Intermediate Similarity	NPC97584
0.7093	Intermediate Similarity	NPC318086
0.7088	Intermediate Similarity	NPC13367
0.7066	Intermediate Similarity	NPC315051
0.7065	Intermediate Similarity	NPC475094
0.7062	Intermediate Similarity	NPC474058
0.7062	Intermediate Similarity	NPC143457
0.7062	Intermediate Similarity	NPC106118
0.7062	Intermediate Similarity	NPC315368
0.7049	Intermediate Similarity	NPC476441
0.7029	Intermediate Similarity	NPC161827
0.7027	Intermediate Similarity	NPC469896
0.7022	Intermediate Similarity	NPC472121
0.702	Intermediate Similarity	NPC277350
0.701	Intermediate Similarity	NPC100863
0.701	Intermediate Similarity	NPC15384
0.701	Intermediate Similarity	NPC244425
0.7	Intermediate Similarity	NPC478158
0.6966	Remote Similarity	NPC201424
0.6954	Remote Similarity	NPC475763
0.6949	Remote Similarity	NPC153694
0.6949	Remote Similarity	NPC211525
0.6943	Remote Similarity	NPC243626
0.6939	Remote Similarity	NPC214428
0.6919	Remote Similarity	NPC476326
0.6911	Remote Similarity	NPC22689
0.6911	Remote Similarity	NPC105055
0.691	Remote Similarity	NPC97380
0.691	Remote Similarity	NPC263709
0.691	Remote Similarity	NPC243673
0.691	Remote Similarity	NPC310403
0.691	Remote Similarity	NPC63210
0.691	Remote Similarity	NPC148468
0.6907	Remote Similarity	NPC97100
0.6907	Remote Similarity	NPC473375
0.6904	Remote Similarity	NPC471512
0.6902	Remote Similarity	NPC470548
0.69	Remote Similarity	NPC472538
0.6882	Remote Similarity	NPC321211
0.6878	Remote Similarity	NPC322621
0.6865	Remote Similarity	NPC129624
0.6864	Remote Similarity	NPC130251
0.6853	Remote Similarity	NPC475489
0.6851	Remote Similarity	NPC52059
0.6851	Remote Similarity	NPC470069
0.685	Remote Similarity	NPC225400
0.6842	Remote Similarity	NPC5620
0.6833	Remote Similarity	NPC85651
0.6829	Remote Similarity	NPC478157
0.6824	Remote Similarity	NPC186284
0.6824	Remote Similarity	NPC22082
0.6823	Remote Similarity	NPC473569
0.6816	Remote Similarity	NPC470786
0.6816	Remote Similarity	NPC471155
0.6812	Remote Similarity	NPC281049
0.6812	Remote Similarity	NPC248601
0.6804	Remote Similarity	NPC275134
0.6804	Remote Similarity	NPC265592
0.6802	Remote Similarity	NPC472103
0.68	Remote Similarity	NPC473376
0.6786	Remote Similarity	NPC472542
0.6786	Remote Similarity	NPC472541
0.6786	Remote Similarity	NPC471199
0.6786	Remote Similarity	NPC267508
0.6786	Remote Similarity	NPC162440
0.6782	Remote Similarity	NPC270241
0.6782	Remote Similarity	NPC212799
0.678	Remote Similarity	NPC471663
0.6779	Remote Similarity	NPC219397
0.6769	Remote Similarity	NPC230313
0.6761	Remote Similarity	NPC243756
0.6758	Remote Similarity	NPC24661
0.6758	Remote Similarity	NPC44357
0.6757	Remote Similarity	NPC298851
0.6757	Remote Similarity	NPC293255
0.6757	Remote Similarity	NPC181138
0.6757	Remote Similarity	NPC21752
0.6757	Remote Similarity	NPC276993
0.6757	Remote Similarity	NPC210415
0.6754	Remote Similarity	NPC282092
0.6736	Remote Similarity	NPC5630
0.6735	Remote Similarity	NPC470787
0.6735	Remote Similarity	NPC472539
0.6735	Remote Similarity	NPC472540
0.673	Remote Similarity	NPC64216
0.672	Remote Similarity	NPC476428
0.6707	Remote Similarity	NPC145754
0.6707	Remote Similarity	NPC239990
0.6707	Remote Similarity	NPC105114
0.6707	Remote Similarity	NPC152850
0.6707	Remote Similarity	NPC89923
0.6707	Remote Similarity	NPC71933
0.6703	Remote Similarity	NPC138293
0.6703	Remote Similarity	NPC113056
0.6702	Remote Similarity	NPC473007
0.6702	Remote Similarity	NPC219336
0.6701	Remote Similarity	NPC22476
0.6701	Remote Similarity	NPC203628
0.67	Remote Similarity	NPC1464

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 NPC285622 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	412
0.2-0.3	655
0.3-0.4	1555
0.4-0.5	3753
0.5-0.6	2236
0.6-0.7	373
0.7-0.8	17
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7758	Intermediate Similarity	NPD5942	Approved
0.7758	Intermediate Similarity	NPD5941	Approved
0.7654	Intermediate Similarity	NPD3625	Discontinued
0.7349	Intermediate Similarity	NPD5024	Approved
0.7299	Intermediate Similarity	NPD7599	Phase 2
0.7257	Intermediate Similarity	NPD7600	Phase 2
0.7234	Intermediate Similarity	NPD8240	Discontinued
0.7184	Intermediate Similarity	NPD7105	Phase 1
0.7175	Intermediate Similarity	NPD3790	Phase 2
0.7165	Intermediate Similarity	NPD6238	Discontinued
0.7117	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6073	Approved
0.7081	Intermediate Similarity	NPD4177	Approved
0.7081	Intermediate Similarity	NPD4175	Approved
0.7073	Intermediate Similarity	NPD4153	Approved
0.7048	Intermediate Similarity	NPD6294	Approved
0.7048	Intermediate Similarity	NPD6295	Approved
0.7045	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1663	Discontinued
0.6988	Remote Similarity	NPD5725	Approved
0.697	Remote Similarity	NPD5184	Approved
0.697	Remote Similarity	NPD5185	Approved
0.697	Remote Similarity	NPD5182	Approved
0.6949	Remote Similarity	NPD8630	Approved
0.6923	Remote Similarity	NPD2093	Discontinued
0.6914	Remote Similarity	NPD5993	Phase 1
0.6909	Remote Similarity	NPD5747	Discontinued
0.6895	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7854	Phase 2
0.6829	Remote Similarity	NPD5263	Approved
0.6823	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1801	Approved
0.6782	Remote Similarity	NPD1802	Approved
0.677	Remote Similarity	NPD3071	Approved
0.677	Remote Similarity	NPD3073	Approved
0.677	Remote Similarity	NPD3072	Approved
0.6768	Remote Similarity	NPD3040	Approved
0.6766	Remote Similarity	NPD5296	Approved
0.6758	Remote Similarity	NPD4976	Discontinued
0.6747	Remote Similarity	NPD5581	Approved
0.6746	Remote Similarity	NPD5318	Discontinued
0.6744	Remote Similarity	NPD5265	Approved
0.6744	Remote Similarity	NPD5264	Approved
0.6738	Remote Similarity	NPD5600	Discontinued
0.6727	Remote Similarity	NPD4676	Approved
0.6708	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4762	Approved
0.6708	Remote Similarity	NPD4761	Approved
0.6702	Remote Similarity	NPD5774	Approved
0.6702	Remote Similarity	NPD5775	Approved
0.6702	Remote Similarity	NPD6557	Phase 2
0.6686	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4602	Approved
0.6667	Remote Similarity	NPD5060	Phase 1
0.6667	Remote Similarity	NPD6623	Phase 3
0.6667	Remote Similarity	NPD7606	Phase 3
0.6667	Remote Similarity	NPD5982	Phase 2
0.665	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4499	Approved
0.6649	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4682	Phase 2
0.6647	Remote Similarity	NPD3508	Approved
0.6647	Remote Similarity	NPD2820	Phase 3
0.6631	Remote Similarity	NPD5466	Approved
0.6615	Remote Similarity	NPD5042	Phase 1
0.6613	Remote Similarity	NPD5633	Discontinued
0.6605	Remote Similarity	NPD4176	Approved
0.6605	Remote Similarity	NPD4178	Approved
0.6602	Remote Similarity	NPD7470	Discontinued
0.6591	Remote Similarity	NPD7478	Approved
0.659	Remote Similarity	NPD2365	Approved
0.6587	Remote Similarity	NPD1069	Approved
0.6587	Remote Similarity	NPD1070	Approved
0.6579	Remote Similarity	NPD3989	Phase 3
0.6579	Remote Similarity	NPD6878	Phase 2
0.6579	Remote Similarity	NPD6879	Phase 2
0.6576	Remote Similarity	NPD7036	Phase 3
0.6576	Remote Similarity	NPD7035	Approved
0.6567	Remote Similarity	NPD7973	Discontinued
0.6554	Remote Similarity	NPD4432	Discontinued
0.6545	Remote Similarity	NPD3990	Phase 3
0.6534	Remote Similarity	NPD3509	Approved
0.6534	Remote Similarity	NPD3510	Approved
0.6527	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD9539	Approved
0.6524	Remote Similarity	NPD9541	Approved
0.6524	Remote Similarity	NPD4677	Discontinued
0.6514	Remote Similarity	NPD7487	Discontinued
0.65	Remote Similarity	NPD2790	Discontinued
0.65	Remote Similarity	NPD5991	Approved
0.65	Remote Similarity	NPD4120	Approved
0.65	Remote Similarity	NPD5990	Approved
0.65	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4121	Phase 3
0.6498	Remote Similarity	NPD7824	Approved
0.6491	Remote Similarity	NPD7510	Approved
0.6489	Remote Similarity	NPD5997	Discontinued
0.6488	Remote Similarity	NPD4794	Discontinued
0.6482	Remote Similarity	NPD3964	Approved
0.6464	Remote Similarity	NPD5743	Approved
0.6464	Remote Similarity	NPD5742	Approved
0.6464	Remote Similarity	NPD5741	Approved
0.6463	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6343	Approved
0.646	Remote Similarity	NPD6345	Approved
0.6453	Remote Similarity	NPD6358	Phase 2
0.6453	Remote Similarity	NPD4126	Approved
0.6448	Remote Similarity	NPD33	Approved
0.6448	Remote Similarity	NPD4393	Approved
0.6446	Remote Similarity	NPD9540	Approved
0.6444	Remote Similarity	NPD3399	Approved
0.6442	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.644	Remote Similarity	NPD7775	Approved
0.6436	Remote Similarity	NPD4600	Approved
0.6436	Remote Similarity	NPD4601	Approved
0.6436	Remote Similarity	NPD6519	Phase 2
0.6436	Remote Similarity	NPD6805	Discontinued
0.6429	Remote Similarity	NPD6571	Approved
0.6429	Remote Similarity	NPD4365	Phase 2
0.6429	Remote Similarity	NPD6570	Approved
0.6421	Remote Similarity	NPD4091	Approved
0.642	Remote Similarity	NPD5918	Discontinued
0.6412	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD7950	Approved
0.6409	Remote Similarity	NPD7791	Approved
0.6409	Remote Similarity	NPD7953	Approved
0.6409	Remote Similarity	NPD7952	Approved
0.6409	Remote Similarity	NPD7790	Approved
0.6409	Remote Similarity	NPD7789	Approved
0.6409	Remote Similarity	NPD7951	Approved
0.6408	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD4151	Approved
0.6406	Remote Similarity	NPD7730	Approved
0.6406	Remote Similarity	NPD7731	Approved
0.6402	Remote Similarity	NPD750	Phase 2
0.64	Remote Similarity	NPD6768	Approved
0.6391	Remote Similarity	NPD4781	Approved
0.6391	Remote Similarity	NPD4783	Approved
0.6389	Remote Similarity	NPD7271	Approved
0.6387	Remote Similarity	NPD3992	Approved
0.6387	Remote Similarity	NPD4092	Approved
0.6387	Remote Similarity	NPD3996	Approved
0.6387	Remote Similarity	NPD3994	Approved
0.6387	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD3991	Approved
0.6387	Remote Similarity	NPD3993	Approved
0.6387	Remote Similarity	NPD3995	Approved
0.6386	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5183	Approved
0.6383	Remote Similarity	NPD5186	Approved
0.6379	Remote Similarity	NPD7511	Approved
0.6379	Remote Similarity	NPD7512	Approved
0.6374	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7528	Approved
0.6368	Remote Similarity	NPD8271	Discontinued
0.6364	Remote Similarity	NPD2584	Suspended
0.6358	Remote Similarity	NPD2994	Approved
0.6355	Remote Similarity	NPD4501	Approved
0.6355	Remote Similarity	NPD4500	Approved
0.6354	Remote Similarity	NPD3998	Approved
0.6354	Remote Similarity	NPD3997	Approved
0.6354	Remote Similarity	NPD3248	Phase 1
0.6354	Remote Similarity	NPD3999	Approved
0.6354	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7881	Approved
0.6352	Remote Similarity	NPD5180	Approved
0.6352	Remote Similarity	NPD5179	Approved
0.6352	Remote Similarity	NPD5181	Approved
0.6341	Remote Similarity	NPD6176	Phase 1
0.634	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5856	Discontinued
0.6335	Remote Similarity	NPD6069	Approved
0.6335	Remote Similarity	NPD6070	Approved
0.6333	Remote Similarity	NPD5748	Phase 2
0.6332	Remote Similarity	NPD6665	Discontinued
0.633	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3983	Phase 3
0.633	Remote Similarity	NPD7890	Discontinued
0.6322	Remote Similarity	NPD1110	Approved
0.6322	Remote Similarity	NPD1109	Approved
0.6318	Remote Similarity	NPD7688	Phase 1
0.6316	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2817	Discontinued
0.6316	Remote Similarity	NPD1527	Phase 2
0.6313	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4796	Discontinued
0.6307	Remote Similarity	NPD6566	Discontinued
0.6301	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7781	Approved
0.6301	Remote Similarity	NPD7780	Approved
0.6296	Remote Similarity	NPD2116	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