NPASS Compound

Structure

NPC192270 OpenBabel07101719132D 31 33 0 0 1 0 0 0 0 0999 V2000 -3.9811 -4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6150 -4.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6150 -3.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5495 3.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0495 2.3512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9811 -4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 -0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 -1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 -0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 0.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1835 -0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 -1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 -2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 1.3512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9811 -3.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4811 -4.0975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0495 2.3512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 2.8512 0.0000 Cl 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 -3.9756 -3.1270 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 -0.4158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.9156 0.8512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3164 1.2784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 23 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 18 2 0 0 0 0 13 2 1 6 0 0 0 13 21 1 0 0 0 0 13 26 1 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 16 20 2 0 0 0 0 17 27 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 0 0 0 0 19 24 1 0 0 0 0 19 29 1 1 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 21 28 2 0 0 0 0 21 30 1 0 0 0 0 22 26 2 0 0 0 0 22 31 1 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	443.2
Volume:	451.471
LogP:	4.02
LogD:	3.177
LogS:	-4.087
# Rotatable Bonds:	7
TPSA:	102.0
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	4.03
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.476
MDCK Permeability:	1.4773573639104143e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.339
Human Intestinal Absorption (HIA):	0.385
20% Bioavailability (F20%):	0.868
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	99.38340759277344%
Volume Distribution (VD):	0.223
Pgp-substrate:	1.3861415386199951%

ADMET: Metabolism

CYP1A2-inhibitor:	0.22
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.474
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.81
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.795
CYP2D6-substrate:	0.775
CYP3A4-inhibitor:	0.747
CYP3A4-substrate:	0.87

ADMET: Excretion

Clearance (CL):	3.201
Half-life (T1/2):	0.56

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.097
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC192270

Natural Product ID:	NPC192270
*Common Name:**	Variecolorin A
IUPAC Name:	(3Z,6S)-3-[[5-[(2R)-3-chloro-2-hydroxy-3-methylbutyl]-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]-6-methylpiperazine-2,5-dione
Synonyms:
Standard InCHIKey:	DKFVASQTSIAAEU-RKFKHAPCSA-N
Standard InCHI:	InChI=1S/C24H30ClN3O3/c1-7-23(3,4)20-16(12-18-22(31)26-13(2)21(30)28-18)15-10-14(8-9-17(15)27-20)11-19(29)24(5,6)25/h7-10,12-13,19,27,29H,1,11H2,2-6H3,(H,26,31)(H,28,30)/b18-12-/t13-,19+/m0/s1
SMILES:	C=CC(c1[nH]c2c(c1/C=C/1N=C(O)[C@@H](N=C1O)C)cc(cc2)C[C@H](C(Cl)(C)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400169
PubChem CID:	23655345
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

*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
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00010a040]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17896816]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17965475]

☑ 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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	50000.0	nM	PMID[470797]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[470797]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000.0	nM	PMID[470797]
NPT35	Others	n.a.		IC50	=	79000.0	nM	PMID[470797]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[470797]

☑ 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 NPC192270 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	1749
0.2-0.3	12533
0.3-0.4	19088
0.4-0.5	4594
0.5-0.6	2652
0.6-0.7	1404
0.7-0.8	319
0.8-0.85	11
0.85-0.9	17
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC293472
0.9627	High Similarity	NPC34508
0.9394	High Similarity	NPC270009
0.939	High Similarity	NPC288785
0.8935	High Similarity	NPC472443
0.8882	High Similarity	NPC38736
0.8851	High Similarity	NPC46413
0.8841	High Similarity	NPC16667
0.8779	High Similarity	NPC472444
0.8765	High Similarity	NPC470507
0.8735	High Similarity	NPC470508
0.8647	High Similarity	NPC472586
0.8634	High Similarity	NPC124005
0.8634	High Similarity	NPC187951
0.8634	High Similarity	NPC37548
0.8606	High Similarity	NPC67056
0.8598	High Similarity	NPC285469
0.858	High Similarity	NPC280548
0.8554	High Similarity	NPC473320
0.8537	High Similarity	NPC207726
0.8421	Intermediate Similarity	NPC6982
0.8415	Intermediate Similarity	NPC32200
0.8395	Intermediate Similarity	NPC129042
0.8385	Intermediate Similarity	NPC242556
0.8373	Intermediate Similarity	NPC184476
0.8343	Intermediate Similarity	NPC472587
0.8313	Intermediate Similarity	NPC471458
0.8263	Intermediate Similarity	NPC141353
0.8249	Intermediate Similarity	NPC19679
0.8198	Intermediate Similarity	NPC154293
0.8129	Intermediate Similarity	NPC271734
0.8043	Intermediate Similarity	NPC474177
0.8035	Intermediate Similarity	NPC54988
0.8035	Intermediate Similarity	NPC474561
0.8035	Intermediate Similarity	NPC49954
0.8034	Intermediate Similarity	NPC198339
0.8023	Intermediate Similarity	NPC311276
0.8023	Intermediate Similarity	NPC194640
0.8023	Intermediate Similarity	NPC151939
0.8011	Intermediate Similarity	NPC189812
0.8011	Intermediate Similarity	NPC329688
0.8	Intermediate Similarity	NPC133366
0.7989	Intermediate Similarity	NPC201700
0.7967	Intermediate Similarity	NPC317030
0.7965	Intermediate Similarity	NPC282231
0.7907	Intermediate Similarity	NPC279918
0.7895	Intermediate Similarity	NPC299594
0.7895	Intermediate Similarity	NPC469762
0.7886	Intermediate Similarity	NPC63751
0.7886	Intermediate Similarity	NPC317430
0.7876	Intermediate Similarity	NPC61637
0.7869	Intermediate Similarity	NPC204565
0.7861	Intermediate Similarity	NPC205403
0.7853	Intermediate Similarity	NPC97525
0.7836	Intermediate Similarity	NPC469785
0.7833	Intermediate Similarity	NPC300688
0.7826	Intermediate Similarity	NPC65215
0.7826	Intermediate Similarity	NPC173028
0.7821	Intermediate Similarity	NPC68354
0.7816	Intermediate Similarity	NPC102423
0.7816	Intermediate Similarity	NPC40779
0.7797	Intermediate Similarity	NPC470498
0.7797	Intermediate Similarity	NPC158129
0.779	Intermediate Similarity	NPC314394
0.7784	Intermediate Similarity	NPC95783
0.7778	Intermediate Similarity	NPC176199
0.7778	Intermediate Similarity	NPC215795
0.7778	Intermediate Similarity	NPC72980
0.776	Intermediate Similarity	NPC476319
0.7753	Intermediate Similarity	NPC313791
0.7753	Intermediate Similarity	NPC472123
0.7747	Intermediate Similarity	NPC472108
0.7747	Intermediate Similarity	NPC139291
0.7747	Intermediate Similarity	NPC163055
0.7737	Intermediate Similarity	NPC476175
0.773	Intermediate Similarity	NPC34271
0.7727	Intermediate Similarity	NPC160105
0.7719	Intermediate Similarity	NPC73952
0.7719	Intermediate Similarity	NPC469760
0.7719	Intermediate Similarity	NPC259644
0.7719	Intermediate Similarity	NPC469786
0.7719	Intermediate Similarity	NPC25008
0.7719	Intermediate Similarity	NPC469763
0.7719	Intermediate Similarity	NPC469765
0.7717	Intermediate Similarity	NPC474707
0.7709	Intermediate Similarity	NPC37423
0.7709	Intermediate Similarity	NPC275305
0.7705	Intermediate Similarity	NPC190007
0.7701	Intermediate Similarity	NPC131718
0.7692	Intermediate Similarity	NPC302191
0.7688	Intermediate Similarity	NPC206967
0.768	Intermediate Similarity	NPC88363
0.7674	Intermediate Similarity	NPC212376
0.7674	Intermediate Similarity	NPC211572
0.7674	Intermediate Similarity	NPC70922
0.7674	Intermediate Similarity	NPC80597
0.7674	Intermediate Similarity	NPC75540
0.7663	Intermediate Similarity	NPC94943
0.7656	Intermediate Similarity	NPC300183
0.765	Intermediate Similarity	NPC48938
0.7644	Intermediate Similarity	NPC230869
0.764	Intermediate Similarity	NPC22079
0.7632	Intermediate Similarity	NPC232130
0.7624	Intermediate Similarity	NPC59269
0.7624	Intermediate Similarity	NPC248454
0.7624	Intermediate Similarity	NPC326575
0.7614	Intermediate Similarity	NPC475422
0.7614	Intermediate Similarity	NPC476118
0.7602	Intermediate Similarity	NPC105818
0.7602	Intermediate Similarity	NPC24678
0.7596	Intermediate Similarity	NPC233936
0.7592	Intermediate Similarity	NPC473747
0.7577	Intermediate Similarity	NPC98715
0.7568	Intermediate Similarity	NPC473189
0.7556	Intermediate Similarity	NPC314603
0.7554	Intermediate Similarity	NPC212535
0.7542	Intermediate Similarity	NPC194411
0.754	Intermediate Similarity	NPC246700
0.7539	Intermediate Similarity	NPC229332
0.7526	Intermediate Similarity	NPC181502
0.7526	Intermediate Similarity	NPC85066
0.7514	Intermediate Similarity	NPC165201
0.7514	Intermediate Similarity	NPC472294
0.7513	Intermediate Similarity	NPC87755
0.7513	Intermediate Similarity	NPC314957
0.7513	Intermediate Similarity	NPC258062
0.7513	Intermediate Similarity	NPC249040
0.7513	Intermediate Similarity	NPC127677
0.75	Intermediate Similarity	NPC314333
0.75	Intermediate Similarity	NPC476106
0.7487	Intermediate Similarity	NPC119700
0.7486	Intermediate Similarity	NPC213468
0.7486	Intermediate Similarity	NPC6093
0.7486	Intermediate Similarity	NPC133261
0.7485	Intermediate Similarity	NPC475450
0.7485	Intermediate Similarity	NPC179365
0.7473	Intermediate Similarity	NPC134586
0.7471	Intermediate Similarity	NPC159856
0.7471	Intermediate Similarity	NPC314372
0.7462	Intermediate Similarity	NPC225821
0.7462	Intermediate Similarity	NPC46225
0.7461	Intermediate Similarity	NPC128823
0.746	Intermediate Similarity	NPC243716
0.7459	Intermediate Similarity	NPC472110
0.7459	Intermediate Similarity	NPC472109
0.7448	Intermediate Similarity	NPC70956
0.7448	Intermediate Similarity	NPC243834
0.744	Intermediate Similarity	NPC2949
0.7432	Intermediate Similarity	NPC211997
0.7423	Intermediate Similarity	NPC475151
0.7423	Intermediate Similarity	NPC470497
0.7419	Intermediate Similarity	NPC165495
0.7409	Intermediate Similarity	NPC306376
0.7407	Intermediate Similarity	NPC329858
0.74	Intermediate Similarity	NPC250129
0.74	Intermediate Similarity	NPC204303
0.7399	Intermediate Similarity	NPC33421
0.7398	Intermediate Similarity	NPC477135
0.738	Intermediate Similarity	NPC163421
0.738	Intermediate Similarity	NPC188387
0.738	Intermediate Similarity	NPC314002
0.738	Intermediate Similarity	NPC15102
0.7377	Intermediate Similarity	NPC203754
0.7377	Intermediate Similarity	NPC150048
0.7366	Intermediate Similarity	NPC176127
0.7362	Intermediate Similarity	NPC473587
0.7358	Intermediate Similarity	NPC153042
0.7354	Intermediate Similarity	NPC128751
0.7353	Intermediate Similarity	NPC190296
0.7351	Intermediate Similarity	NPC91179
0.735	Intermediate Similarity	NPC475165
0.7345	Intermediate Similarity	NPC92796
0.7345	Intermediate Similarity	NPC135141
0.7344	Intermediate Similarity	NPC195314
0.734	Intermediate Similarity	NPC171171
0.7337	Intermediate Similarity	NPC475910
0.7333	Intermediate Similarity	NPC109447
0.733	Intermediate Similarity	NPC99666
0.733	Intermediate Similarity	NPC55493
0.7326	Intermediate Similarity	NPC84478
0.7326	Intermediate Similarity	NPC204717
0.732	Intermediate Similarity	NPC470499
0.732	Intermediate Similarity	NPC265576
0.7317	Intermediate Similarity	NPC475428
0.7316	Intermediate Similarity	NPC469497
0.7316	Intermediate Similarity	NPC469501
0.7316	Intermediate Similarity	NPC106833
0.7316	Intermediate Similarity	NPC469470
0.7305	Intermediate Similarity	NPC325252
0.7301	Intermediate Similarity	NPC473762
0.73	Intermediate Similarity	NPC271862
0.7297	Intermediate Similarity	NPC219336
0.7294	Intermediate Similarity	NPC473868
0.7294	Intermediate Similarity	NPC63157
0.7283	Intermediate Similarity	NPC21605
0.7283	Intermediate Similarity	NPC267885
0.7283	Intermediate Similarity	NPC24594
0.7283	Intermediate Similarity	NPC472122
0.7282	Intermediate Similarity	NPC241024
0.7277	Intermediate Similarity	NPC87856

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 NPC192270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	566
0.2-0.3	827
0.3-0.4	1465
0.4-0.5	2998
0.5-0.6	2451
0.6-0.7	598
0.7-0.8	71
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8363	Intermediate Similarity	NPD1326	Approved
0.8363	Intermediate Similarity	NPD1325	Approved
0.7966	Intermediate Similarity	NPD2382	Approved
0.7966	Intermediate Similarity	NPD2381	Approved
0.7966	Intermediate Similarity	NPD2380	Approved
0.7965	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4079	Approved
0.7877	Intermediate Similarity	NPD8386	Phase 2
0.7877	Intermediate Similarity	NPD4076	Approved
0.7821	Intermediate Similarity	NPD3505	Approved
0.7821	Intermediate Similarity	NPD2144	Approved
0.7821	Intermediate Similarity	NPD3506	Approved
0.7818	Intermediate Similarity	NPD1592	Phase 3
0.7811	Intermediate Similarity	NPD4462	Approved
0.7811	Intermediate Similarity	NPD4463	Approved
0.7753	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD5596	Phase 2
0.7746	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD5065	Approved
0.7692	Intermediate Similarity	NPD3038	Discontinued
0.7688	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD6595	Phase 3
0.7614	Intermediate Similarity	NPD5138	Approved
0.7614	Intermediate Similarity	NPD5140	Approved
0.7584	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5021	Discontinued
0.7568	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD4511	Phase 1
0.7558	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6158	Phase 2
0.7544	Intermediate Similarity	NPD3100	Discontinued
0.75	Intermediate Similarity	NPD4499	Approved
0.7486	Intermediate Similarity	NPD4639	Approved
0.7486	Intermediate Similarity	NPD4638	Approved
0.7486	Intermediate Similarity	NPD4640	Approved
0.7457	Intermediate Similarity	NPD2882	Phase 1
0.7446	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD2172	Phase 1
0.7394	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD8431	Approved
0.7394	Intermediate Similarity	NPD2383	Phase 1
0.7389	Intermediate Similarity	NPD2844	Phase 3
0.7382	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5901	Discontinued
0.7358	Intermediate Similarity	NPD7948	Phase 1
0.732	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5254	Discontinued
0.7277	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5913	Phase 3
0.7277	Intermediate Similarity	NPD4699	Discontinued
0.7273	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3525	Discontinued
0.725	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD4601	Approved
0.7245	Intermediate Similarity	NPD4600	Approved
0.7243	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3003	Approved
0.7236	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD482	Approved
0.7228	Intermediate Similarity	NPD6492	Phase 2
0.7225	Intermediate Similarity	NPD2564	Approved
0.7225	Intermediate Similarity	NPD2565	Phase 2
0.7216	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3835	Phase 3
0.72	Intermediate Similarity	NPD3833	Phase 3
0.7194	Intermediate Similarity	NPD2175	Phase 3
0.7194	Intermediate Similarity	NPD2176	Approved
0.7194	Intermediate Similarity	NPD2177	Approved
0.7192	Intermediate Similarity	NPD3330	Phase 1
0.7189	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4703	Approved
0.7184	Intermediate Similarity	NPD4702	Approved
0.7181	Intermediate Similarity	NPD2095	Phase 2
0.7181	Intermediate Similarity	NPD2092	Phase 2
0.7181	Intermediate Similarity	NPD2094	Phase 2
0.7179	Intermediate Similarity	NPD5003	Discontinued
0.7176	Intermediate Similarity	NPD786	Approved
0.7173	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD5899	Approved
0.7166	Intermediate Similarity	NPD5898	Approved
0.7166	Intermediate Similarity	NPD5897	Approved
0.7151	Intermediate Similarity	NPD6159	Phase 2
0.715	Intermediate Similarity	NPD3404	Approved
0.7143	Intermediate Similarity	NPD2096	Phase 2
0.7143	Intermediate Similarity	NPD2091	Phase 2
0.7135	Intermediate Similarity	NPD4128	Approved
0.7128	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1683	Approved
0.7113	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1038	Approved
0.7107	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1768	Approved
0.7101	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5100	Phase 3
0.709	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1534	Approved
0.7065	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7957	Phase 1
0.7059	Intermediate Similarity	NPD5939	Approved
0.7059	Intermediate Similarity	NPD5936	Approved
0.705	Intermediate Similarity	NPD6176	Phase 1
0.7045	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3961	Discontinued
0.703	Intermediate Similarity	NPD8322	Phase 2
0.7027	Intermediate Similarity	NPD3117	Approved
0.7027	Intermediate Similarity	NPD3116	Approved
0.702	Intermediate Similarity	NPD3814	Phase 1
0.7017	Intermediate Similarity	NPD1404	Approved
0.7017	Intermediate Similarity	NPD1403	Approved
0.7016	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2641	Approved
0.7011	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2640	Approved
0.7005	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4075	Phase 2
0.7	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1722	Approved
0.6989	Remote Similarity	NPD750	Phase 2
0.6985	Remote Similarity	NPD484	Approved
0.6979	Remote Similarity	NPD6217	Discontinued
0.6976	Remote Similarity	NPD5067	Phase 2
0.6976	Remote Similarity	NPD5066	Phase 2
0.6976	Remote Similarity	NPD7470	Discontinued
0.6976	Remote Similarity	NPD6220	Phase 3
0.697	Remote Similarity	NPD2727	Phase 2
0.6961	Remote Similarity	NPD5255	Approved
0.6959	Remote Similarity	NPD6281	Approved
0.6957	Remote Similarity	NPD2642	Approved
0.6957	Remote Similarity	NPD2639	Approved
0.6954	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7935	Phase 2
0.6943	Remote Similarity	NPD4948	Discontinued
0.6942	Remote Similarity	NPD8093	Discontinued
0.6935	Remote Similarity	NPD6249	Phase 2
0.6935	Remote Similarity	NPD6248	Phase 2
0.6931	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5612	Discontinued
0.6916	Remote Similarity	NPD6978	Phase 2
0.6916	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5104	Approved
0.6911	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD2915	Discontinued
0.6901	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4501	Approved
0.69	Remote Similarity	NPD4500	Approved
0.6897	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6452	Discontinued
0.6889	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD4909	Approved
0.6886	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6846	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD2920	Discontinued
0.6881	Remote Similarity	NPD8072	Approved
0.6878	Remote Similarity	NPD4181	Approved
0.6878	Remote Similarity	NPD8123	Approved
0.6878	Remote Similarity	NPD8122	Approved
0.6875	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5903	Approved
0.6875	Remote Similarity	NPD5902	Approved
0.6875	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1392	Approved
0.6863	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1262	Discovery
0.6859	Remote Similarity	NPD4203	Approved
0.6859	Remote Similarity	NPD4204	Approved
0.6856	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD802	Phase 2
0.6848	Remote Similarity	NPD3323	Discontinued
0.6847	Remote Similarity	NPD8272	Phase 2
0.6845	Remote Similarity	NPD3654	Approved
0.6845	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3082	Discontinued
0.6832	Remote Similarity	NPD8073	Approved
0.6829	Remote Similarity	NPD2510	Approved
0.6829	Remote Similarity	NPD2509	Approved
0.6828	Remote Similarity	NPD5862	Discovery
0.6827	Remote Similarity	NPD8094	Discontinued
0.6826	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5471	Phase 3
0.6821	Remote Similarity	NPD4334	Discontinued
0.6818	Remote Similarity	NPD7944	Discontinued
0.6818	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2077	Approved
0.6809	Remote Similarity	NPD7418	Discontinued
0.6809	Remote Similarity	NPD2076	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