NPASS Compound

Structure

NPC34508 OpenBabel07101718282D 30 32 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 4.1835 -2.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9156 -2.8512 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 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 5.0495 -2.3512 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 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 2 13 2 0 0 0 0 3 13 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 24 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 14 4 1 6 0 0 0 14 22 1 0 0 0 0 14 25 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 21 2 0 0 0 0 18 26 1 0 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 1 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 22 29 1 0 0 0 0 23 25 2 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	407.22
Volume:	433.624
LogP:	3.426
LogD:	2.615
LogS:	-4.051
# Rotatable Bonds:	7
TPSA:	102.0
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.447
Synthetic Accessibility Score:	3.942
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.468
MDCK Permeability:	1.1380264368199278e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.414
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	97.6408462524414%
Volume Distribution (VD):	0.397
Pgp-substrate:	2.2882540225982666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.239
CYP1A2-substrate:	0.884
CYP2C19-inhibitor:	0.293
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.618
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.661
CYP2D6-substrate:	0.688
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.749

ADMET: Excretion

Clearance (CL):	3.32
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.521
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.091
Carcinogencity:	0.123
Eye Corrosion:	0.003
Eye Irritation:	0.016
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: NPC34508

Natural Product ID:	NPC34508
*Common Name:**	Variecolorin C
IUPAC Name:	(3Z,6S)-3-[[5-[(2R)-2-hydroxy-3-methylbut-3-enyl]-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]-6-methylpiperazine-2,5-dione
Synonyms:	Variecolorin C
Standard InCHIKey:	SEQDZBXCPJTKIR-GTUZUVEESA-N
Standard InCHI:	InChI=1S/C24H29N3O3/c1-7-24(5,6)21-17(12-19-23(30)25-14(4)22(29)27-19)16-10-15(8-9-18(16)26-21)11-20(28)13(2)3/h7-10,12,14,20,26,28H,1-2,11H2,3-6H3,(H,25,30)(H,27,29)/b19-12-/t14-,20+/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(=C)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL250874
PubChem CID:	23634522
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[473720]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[473720]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000.0	nM	PMID[473720]
NPT35	Others	n.a.		IC50	=	75000.0	nM	PMID[473720]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[473720]

☑ 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 NPC34508 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	306
0.1-0.2	1612
0.2-0.3	11409
0.3-0.4	19272
0.4-0.5	5249
0.5-0.6	2818
0.6-0.7	1485
0.7-0.8	486
0.8-0.85	34
0.85-0.9	14
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC270009
0.9627	High Similarity	NPC192270
0.9321	High Similarity	NPC293472
0.9264	High Similarity	NPC472443
0.9226	High Similarity	NPC38736
0.9177	High Similarity	NPC16667
0.9167	High Similarity	NPC46413
0.9103	High Similarity	NPC470507
0.9096	High Similarity	NPC472444
0.9062	High Similarity	NPC470508
0.9024	High Similarity	NPC288785
0.8968	High Similarity	NPC124005
0.8968	High Similarity	NPC187951
0.8968	High Similarity	NPC37548
0.8963	High Similarity	NPC472586
0.8931	High Similarity	NPC67056
0.8924	High Similarity	NPC285469
0.8896	High Similarity	NPC280548
0.8875	High Similarity	NPC473320
0.8861	High Similarity	NPC207726
0.8727	High Similarity	NPC6982
0.8718	High Similarity	NPC129042
0.871	High Similarity	NPC242556
0.8701	High Similarity	NPC32200
0.8688	High Similarity	NPC184476
0.865	High Similarity	NPC472587
0.8625	High Similarity	NPC471458
0.8571	High Similarity	NPC141353
0.8538	High Similarity	NPC19679
0.8494	Intermediate Similarity	NPC154293
0.8424	Intermediate Similarity	NPC271734
0.8323	Intermediate Similarity	NPC54988
0.8323	Intermediate Similarity	NPC474561
0.8323	Intermediate Similarity	NPC49954
0.8315	Intermediate Similarity	NPC474177
0.8314	Intermediate Similarity	NPC198339
0.8313	Intermediate Similarity	NPC311276
0.8313	Intermediate Similarity	NPC194640
0.8304	Intermediate Similarity	NPC151939
0.8294	Intermediate Similarity	NPC329688
0.8294	Intermediate Similarity	NPC189812
0.8274	Intermediate Similarity	NPC201700
0.8268	Intermediate Similarity	NPC133366
0.8253	Intermediate Similarity	NPC282231
0.8239	Intermediate Similarity	NPC317030
0.8193	Intermediate Similarity	NPC279918
0.8182	Intermediate Similarity	NPC469762
0.8182	Intermediate Similarity	NPC299594
0.8166	Intermediate Similarity	NPC317430
0.8166	Intermediate Similarity	NPC63751
0.8136	Intermediate Similarity	NPC204565
0.8129	Intermediate Similarity	NPC97525
0.8122	Intermediate Similarity	NPC205403
0.8121	Intermediate Similarity	NPC469785
0.8103	Intermediate Similarity	NPC300688
0.8095	Intermediate Similarity	NPC40779
0.8095	Intermediate Similarity	NPC102423
0.8092	Intermediate Similarity	NPC68354
0.809	Intermediate Similarity	NPC65215
0.809	Intermediate Similarity	NPC173028
0.807	Intermediate Similarity	NPC470498
0.807	Intermediate Similarity	NPC158129
0.8057	Intermediate Similarity	NPC314394
0.8046	Intermediate Similarity	NPC176199
0.8046	Intermediate Similarity	NPC215795
0.8046	Intermediate Similarity	NPC72980
0.8045	Intermediate Similarity	NPC95783
0.8023	Intermediate Similarity	NPC476319
0.8023	Intermediate Similarity	NPC472123
0.8023	Intermediate Similarity	NPC313791
0.8011	Intermediate Similarity	NPC139291
0.8011	Intermediate Similarity	NPC472108
0.8011	Intermediate Similarity	NPC163055
0.8	Intermediate Similarity	NPC73952
0.8	Intermediate Similarity	NPC259644
0.8	Intermediate Similarity	NPC469763
0.8	Intermediate Similarity	NPC469765
0.8	Intermediate Similarity	NPC25008
0.8	Intermediate Similarity	NPC160105
0.8	Intermediate Similarity	NPC469760
0.8	Intermediate Similarity	NPC469786
0.7989	Intermediate Similarity	NPC34271
0.7978	Intermediate Similarity	NPC474707
0.7977	Intermediate Similarity	NPC275305
0.7977	Intermediate Similarity	NPC37423
0.7976	Intermediate Similarity	NPC131718
0.7966	Intermediate Similarity	NPC190007
0.7955	Intermediate Similarity	NPC302191
0.7952	Intermediate Similarity	NPC70922
0.7952	Intermediate Similarity	NPC212376
0.7952	Intermediate Similarity	NPC75540
0.7952	Intermediate Similarity	NPC80597
0.7952	Intermediate Similarity	NPC211572
0.7944	Intermediate Similarity	NPC206967
0.7943	Intermediate Similarity	NPC88363
0.7935	Intermediate Similarity	NPC22079
0.7921	Intermediate Similarity	NPC94943
0.7917	Intermediate Similarity	NPC230869
0.791	Intermediate Similarity	NPC48938
0.7903	Intermediate Similarity	NPC300183
0.7886	Intermediate Similarity	NPC326575
0.7886	Intermediate Similarity	NPC248454
0.7886	Intermediate Similarity	NPC59269
0.7882	Intermediate Similarity	NPC476118
0.788	Intermediate Similarity	NPC232130
0.7879	Intermediate Similarity	NPC24678
0.7879	Intermediate Similarity	NPC105818
0.7853	Intermediate Similarity	NPC233936
0.7853	Intermediate Similarity	NPC475422
0.7838	Intermediate Similarity	NPC473747
0.7821	Intermediate Similarity	NPC473189
0.7819	Intermediate Similarity	NPC98715
0.7816	Intermediate Similarity	NPC314603
0.7809	Intermediate Similarity	NPC212535
0.7803	Intermediate Similarity	NPC194411
0.779	Intermediate Similarity	NPC246700
0.7784	Intermediate Similarity	NPC229332
0.7772	Intermediate Similarity	NPC85066
0.7772	Intermediate Similarity	NPC181502
0.7771	Intermediate Similarity	NPC179365
0.7771	Intermediate Similarity	NPC475450
0.7765	Intermediate Similarity	NPC472294
0.7765	Intermediate Similarity	NPC165201
0.7754	Intermediate Similarity	NPC249040
0.7749	Intermediate Similarity	NPC258062
0.7749	Intermediate Similarity	NPC127677
0.7749	Intermediate Similarity	NPC87755
0.7749	Intermediate Similarity	NPC314957
0.7747	Intermediate Similarity	NPC314333
0.7744	Intermediate Similarity	NPC314372
0.7744	Intermediate Similarity	NPC159856
0.774	Intermediate Similarity	NPC133261
0.774	Intermediate Similarity	NPC6093
0.774	Intermediate Similarity	NPC213468
0.7737	Intermediate Similarity	NPC476106
0.7735	Intermediate Similarity	NPC119700
0.7727	Intermediate Similarity	NPC134586
0.7716	Intermediate Similarity	NPC2949
0.7709	Intermediate Similarity	NPC472109
0.7709	Intermediate Similarity	NPC472110
0.7705	Intermediate Similarity	NPC243716
0.7701	Intermediate Similarity	NPC128823
0.7696	Intermediate Similarity	NPC46225
0.7696	Intermediate Similarity	NPC225821
0.7688	Intermediate Similarity	NPC70956
0.7688	Intermediate Similarity	NPC243834
0.7684	Intermediate Similarity	NPC211997
0.7667	Intermediate Similarity	NPC165495
0.7665	Intermediate Similarity	NPC33421
0.766	Intermediate Similarity	NPC475151
0.766	Intermediate Similarity	NPC470497
0.7656	Intermediate Similarity	NPC61637
0.765	Intermediate Similarity	NPC329858
0.7647	Intermediate Similarity	NPC306376
0.7643	Intermediate Similarity	NPC473587
0.7632	Intermediate Similarity	NPC477135
0.7629	Intermediate Similarity	NPC250129
0.7627	Intermediate Similarity	NPC203754
0.7627	Intermediate Similarity	NPC150048
0.7624	Intermediate Similarity	NPC314002
0.7624	Intermediate Similarity	NPC188387
0.7624	Intermediate Similarity	NPC15102
0.7624	Intermediate Similarity	NPC163421
0.7622	Intermediate Similarity	NPC190296
0.7611	Intermediate Similarity	NPC176127
0.7602	Intermediate Similarity	NPC92796
0.7602	Intermediate Similarity	NPC135141
0.7598	Intermediate Similarity	NPC91179
0.7596	Intermediate Similarity	NPC128751
0.7595	Intermediate Similarity	NPC475428
0.7594	Intermediate Similarity	NPC153042
0.7586	Intermediate Similarity	NPC109447
0.7582	Intermediate Similarity	NPC171171
0.7581	Intermediate Similarity	NPC195314
0.758	Intermediate Similarity	NPC473762
0.7578	Intermediate Similarity	NPC325252
0.7577	Intermediate Similarity	NPC475165
0.7569	Intermediate Similarity	NPC84478
0.7569	Intermediate Similarity	NPC204717
0.7568	Intermediate Similarity	NPC99666
0.7568	Intermediate Similarity	NPC55493
0.7565	Intermediate Similarity	NPC475910
0.7561	Intermediate Similarity	NPC473868
0.7561	Intermediate Similarity	NPC63157
0.7554	Intermediate Similarity	NPC106833
0.7554	Intermediate Similarity	NPC469470
0.7554	Intermediate Similarity	NPC469497
0.7554	Intermediate Similarity	NPC469501
0.7553	Intermediate Similarity	NPC470499
0.7553	Intermediate Similarity	NPC265576
0.7545	Intermediate Similarity	NPC21605
0.7542	Intermediate Similarity	NPC219336
0.7528	Intermediate Similarity	NPC267885
0.7528	Intermediate Similarity	NPC472122
0.7528	Intermediate Similarity	NPC24594
0.7526	Intermediate Similarity	NPC271862
0.7516	Intermediate Similarity	NPC198988
0.7514	Intermediate Similarity	NPC469358
0.7514	Intermediate Similarity	NPC474409
0.7514	Intermediate Similarity	NPC220765

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 NPC34508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	547
0.2-0.3	794
0.3-0.4	1391
0.4-0.5	2865
0.5-0.6	2554
0.6-0.7	699
0.7-0.8	120
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD1326	Approved
0.8667	High Similarity	NPD1325	Approved
0.8246	Intermediate Similarity	NPD2381	Approved
0.8246	Intermediate Similarity	NPD2380	Approved
0.8246	Intermediate Similarity	NPD2382	Approved
0.815	Intermediate Similarity	NPD8386	Phase 2
0.815	Intermediate Similarity	NPD4079	Approved
0.815	Intermediate Similarity	NPD4076	Approved
0.8113	Intermediate Similarity	NPD1592	Phase 3
0.8098	Intermediate Similarity	NPD4462	Approved
0.8098	Intermediate Similarity	NPD4463	Approved
0.8092	Intermediate Similarity	NPD3505	Approved
0.8092	Intermediate Similarity	NPD2144	Approved
0.8092	Intermediate Similarity	NPD3506	Approved
0.8011	Intermediate Similarity	NPD5596	Phase 2
0.7977	Intermediate Similarity	NPD5065	Approved
0.7964	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD3038	Discontinued
0.7941	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6595	Phase 3
0.7882	Intermediate Similarity	NPD5138	Approved
0.7882	Intermediate Similarity	NPD5140	Approved
0.7849	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD5021	Discontinued
0.7831	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6158	Phase 2
0.7821	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD3100	Discontinued
0.7807	Intermediate Similarity	NPD4511	Phase 1
0.7747	Intermediate Similarity	NPD4499	Approved
0.7746	Intermediate Similarity	NPD4640	Approved
0.7746	Intermediate Similarity	NPD4639	Approved
0.7746	Intermediate Similarity	NPD4638	Approved
0.7725	Intermediate Similarity	NPD2882	Phase 1
0.7719	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD2172	Phase 1
0.7644	Intermediate Similarity	NPD2844	Phase 3
0.7637	Intermediate Similarity	NPD2383	Phase 1
0.7637	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8431	Approved
0.7622	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7948	Phase 1
0.7592	Intermediate Similarity	NPD5901	Discontinued
0.7576	Intermediate Similarity	NPD5254	Discontinued
0.7515	Intermediate Similarity	NPD3525	Discontinued
0.7514	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5913	Phase 3
0.7514	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4601	Approved
0.7474	Intermediate Similarity	NPD4600	Approved
0.7472	Intermediate Similarity	NPD6492	Phase 2
0.7472	Intermediate Similarity	NPD482	Approved
0.7461	Intermediate Similarity	NPD3003	Approved
0.7461	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD2564	Approved
0.7459	Intermediate Similarity	NPD2565	Phase 2
0.7456	Intermediate Similarity	NPD3833	Phase 3
0.7456	Intermediate Similarity	NPD3835	Phase 3
0.7447	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4702	Approved
0.744	Intermediate Similarity	NPD4703	Approved
0.7439	Intermediate Similarity	NPD786	Approved
0.743	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2175	Phase 3
0.7421	Intermediate Similarity	NPD2176	Approved
0.7421	Intermediate Similarity	NPD2177	Approved
0.7418	Intermediate Similarity	NPD2092	Phase 2
0.7418	Intermediate Similarity	NPD2094	Phase 2
0.7418	Intermediate Similarity	NPD2095	Phase 2
0.7411	Intermediate Similarity	NPD3330	Phase 1
0.7407	Intermediate Similarity	NPD5003	Discontinued
0.7405	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5897	Approved
0.7403	Intermediate Similarity	NPD5898	Approved
0.7403	Intermediate Similarity	NPD5899	Approved
0.7389	Intermediate Similarity	NPD6159	Phase 2
0.7381	Intermediate Similarity	NPD1683	Approved
0.738	Intermediate Similarity	NPD3404	Approved
0.7377	Intermediate Similarity	NPD2091	Phase 2
0.7377	Intermediate Similarity	NPD2096	Phase 2
0.7374	Intermediate Similarity	NPD4128	Approved
0.7362	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD1038	Approved
0.7333	Intermediate Similarity	NPD5100	Phase 3
0.733	Intermediate Similarity	NPD1768	Approved
0.733	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7957	Phase 1
0.7282	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5939	Approved
0.7273	Intermediate Similarity	NPD5936	Approved
0.7268	Intermediate Similarity	NPD6176	Phase 1
0.7259	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD3961	Discontinued
0.7257	Intermediate Similarity	NPD1403	Approved
0.7257	Intermediate Similarity	NPD1404	Approved
0.7256	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD2641	Approved
0.7247	Intermediate Similarity	NPD2640	Approved
0.7246	Intermediate Similarity	NPD1722	Approved
0.7245	Intermediate Similarity	NPD8322	Phase 2
0.7243	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD3814	Phase 1
0.7238	Intermediate Similarity	NPD4075	Phase 2
0.7222	Intermediate Similarity	NPD750	Phase 2
0.7202	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD484	Approved
0.72	Intermediate Similarity	NPD5255	Approved
0.7191	Intermediate Similarity	NPD2639	Approved
0.7191	Intermediate Similarity	NPD2642	Approved
0.7186	Intermediate Similarity	NPD5067	Phase 2
0.7186	Intermediate Similarity	NPD5066	Phase 2
0.7186	Intermediate Similarity	NPD6220	Phase 3
0.7186	Intermediate Similarity	NPD7470	Discontinued
0.7181	Intermediate Similarity	NPD6281	Approved
0.7173	Intermediate Similarity	NPD7935	Phase 2
0.7166	Intermediate Similarity	NPD4948	Discontinued
0.715	Intermediate Similarity	NPD8093	Discontinued
0.715	Intermediate Similarity	NPD6249	Phase 2
0.715	Intermediate Similarity	NPD6248	Phase 2
0.7143	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5104	Approved
0.7143	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2915	Discontinued
0.7129	Intermediate Similarity	NPD5612	Discontinued
0.7128	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6452	Discontinued
0.7115	Intermediate Similarity	NPD6978	Phase 2
0.7115	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4501	Approved
0.7113	Intermediate Similarity	NPD4500	Approved
0.7108	Intermediate Similarity	NPD1262	Discovery
0.7104	Intermediate Similarity	NPD8123	Approved
0.7104	Intermediate Similarity	NPD8122	Approved
0.7104	Intermediate Similarity	NPD4181	Approved
0.7101	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3654	Approved
0.7098	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2920	Discontinued
0.7092	Intermediate Similarity	NPD8072	Approved
0.7081	Intermediate Similarity	NPD4204	Approved
0.7081	Intermediate Similarity	NPD4203	Approved
0.7081	Intermediate Similarity	NPD995	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5902	Approved
0.7079	Intermediate Similarity	NPD5903	Approved
0.7079	Intermediate Similarity	NPD3323	Discontinued
0.7074	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1392	Approved
0.7071	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD802	Phase 2
0.7059	Intermediate Similarity	NPD3082	Discontinued
0.7056	Intermediate Similarity	NPD5862	Discovery
0.7056	Intermediate Similarity	NPD8272	Phase 2
0.7053	Intermediate Similarity	NPD4699	Discontinued
0.7041	Intermediate Similarity	NPD8073	Approved
0.7041	Intermediate Similarity	NPD5020	Approved
0.7039	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4334	Discontinued
0.7035	Intermediate Similarity	NPD2510	Approved
0.7035	Intermediate Similarity	NPD2509	Approved
0.7033	Intermediate Similarity	NPD7418	Discontinued
0.7031	Intermediate Similarity	NPD7944	Discontinued
0.7031	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8094	Discontinued
0.703	Intermediate Similarity	NPD3385	Approved
0.7022	Intermediate Similarity	NPD1684	Approved
0.7022	Intermediate Similarity	NPD1685	Approved
0.7017	Intermediate Similarity	NPD7474	Suspended
0.701	Intermediate Similarity	NPD7777	Approved
0.701	Intermediate Similarity	NPD53	Approved
0.701	Intermediate Similarity	NPD7778	Approved
0.7005	Intermediate Similarity	NPD4886	Phase 2
0.7005	Intermediate Similarity	NPD4957	Phase 2
0.7	Intermediate Similarity	NPD3717	Discontinued
0.7	Intermediate Similarity	NPD5117	Phase 2
0.6995	Remote Similarity	NPD2928	Phase 2
0.6995	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6026	Approved
0.6976	Remote Similarity	NPD8405	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