NPASS Compound

Structure

NPC32200 OpenBabel07101718202D 34 37 0 0 1 0 0 0 0 0999 V2000 1.9345 5.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5554 -0.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3005 5.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3005 4.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1340 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 5.8147 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3194 2.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2464 0.1080 0.0000 C 0 0 1 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 3.1691 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6284 2.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9345 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2683 0.3160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6065 1.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 4.9487 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9156 0.8512 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 3.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9593 1.2670 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5991 -0.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2757 2.5454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 27 1 0 0 0 0 9 25 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 21 1 0 0 0 0 12 17 1 0 0 0 0 12 20 2 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 2 1 1 0 0 0 14 23 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 17 22 2 0 0 0 0 18 27 1 0 0 0 0 19 29 1 0 0 0 0 20 24 1 0 0 0 0 20 30 1 0 0 0 0 21 26 1 6 0 0 0 21 34 1 0 0 0 0 22 25 1 0 0 0 0 22 29 1 0 0 0 0 23 30 2 0 0 0 0 23 31 1 0 0 0 0 24 28 2 0 0 0 0 24 32 1 0 0 0 0 26 33 1 0 0 0 0 27 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	465.26
Volume:	488.382
LogP:	4.332
LogD:	3.276
LogS:	-3.587
# Rotatable Bonds:	5
TPSA:	111.23
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	4.317
Fsp3:	0.481
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:	-5.313
MDCK Permeability:	1.4218303476809524e-05
Pgp-inhibitor:	0.761
Pgp-substrate:	0.094
Human Intestinal Absorption (HIA):	0.961
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	97.7064437866211%
Volume Distribution (VD):	0.28
Pgp-substrate:	1.9533511400222778%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.568
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.162
CYP2C9-inhibitor:	0.239
CYP2C9-substrate:	0.789
CYP2D6-inhibitor:	0.319
CYP2D6-substrate:	0.358
CYP3A4-inhibitor:	0.527
CYP3A4-substrate:	0.814

ADMET: Excretion

Clearance (CL):	3.126
Half-life (T1/2):	0.494

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.375
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.112
Carcinogencity:	0.476
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC32200

Natural Product ID:	NPC32200
*Common Name:**	Variecolorin K
IUPAC Name:	(3Z,6S)-3-[[(6R)-6-(2-hydroxypropan-2-yl)-8,8-dimethyl-2-(2-methylbut-3-en-2-yl)-5,6-dihydro-1H-pyrano[4,3-f]indol-3-yl]methylidene]-6-methylpiperazine-2,5-dione
Synonyms:	Variecolorin K
Standard InCHIKey:	QFJACXSXSZHCNW-HUHPWQTHSA-N
Standard InCHI:	InChI=1S/C27H35N3O4/c1-9-25(3,4)22-17(12-20-24(32)28-14(2)23(31)30-20)16-10-15-11-21(26(5,6)33)34-27(7,8)18(15)13-19(16)29-22/h9-10,12-14,21,29,33H,1,11H2,2-8H3,(H,28,32)(H,30,31)/b20-12-/t14-,21+/m0/s1
SMILES:	C=CC(C)(C)c1c(/C=C2/C(=N[C@@H](C)C(=N2)O)O)c2cc3C[C@H](C(C)(C)O)OC(C)(C)c3cc2[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251227
PubChem CID:	23655740
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[493745]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[493745]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000.0	nM	PMID[493745]
NPT35	Others	n.a.		IC50	=	89000.0	nM	PMID[493745]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[493745]

☑ 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 NPC32200 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	353
0.1-0.2	1616
0.2-0.3	8987
0.3-0.4	16582
0.4-0.5	9820
0.5-0.6	3388
0.6-0.7	1605
0.7-0.8	326
0.8-0.85	14
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8927	High Similarity	NPC270009
0.8846	High Similarity	NPC46413
0.8778	High Similarity	NPC472444
0.8701	High Similarity	NPC34508
0.8611	High Similarity	NPC472443
0.8444	Intermediate Similarity	NPC472586
0.8415	Intermediate Similarity	NPC192270
0.838	Intermediate Similarity	NPC280548
0.8362	Intermediate Similarity	NPC472587
0.8251	Intermediate Similarity	NPC293472
0.8249	Intermediate Similarity	NPC473320
0.8245	Intermediate Similarity	NPC34271
0.8182	Intermediate Similarity	NPC184476
0.8177	Intermediate Similarity	NPC205403
0.8172	Intermediate Similarity	NPC19679
0.8125	Intermediate Similarity	NPC38736
0.8101	Intermediate Similarity	NPC16667
0.8098	Intermediate Similarity	NPC288785
0.8085	Intermediate Similarity	NPC476319
0.8023	Intermediate Similarity	NPC471458
0.8011	Intermediate Similarity	NPC470508
0.7989	Intermediate Similarity	NPC67056
0.797	Intermediate Similarity	NPC250129
0.7937	Intermediate Similarity	NPC165201
0.7923	Intermediate Similarity	NPC61813
0.7921	Intermediate Similarity	NPC475165
0.7921	Intermediate Similarity	NPC470507
0.7898	Intermediate Similarity	NPC37548
0.7898	Intermediate Similarity	NPC124005
0.7898	Intermediate Similarity	NPC187951
0.7889	Intermediate Similarity	NPC477135
0.7877	Intermediate Similarity	NPC285469
0.7854	Intermediate Similarity	NPC160527
0.7854	Intermediate Similarity	NPC473650
0.7837	Intermediate Similarity	NPC470874
0.7826	Intermediate Similarity	NPC154293
0.7821	Intermediate Similarity	NPC207726
0.7812	Intermediate Similarity	NPC119700
0.7784	Intermediate Similarity	NPC129042
0.7783	Intermediate Similarity	NPC284102
0.7778	Intermediate Similarity	NPC198339
0.7778	Intermediate Similarity	NPC96131
0.7778	Intermediate Similarity	NPC141353
0.7767	Intermediate Similarity	NPC97388
0.775	Intermediate Similarity	NPC123019
0.7742	Intermediate Similarity	NPC6982
0.7739	Intermediate Similarity	NPC475151
0.7732	Intermediate Similarity	NPC95783
0.7723	Intermediate Similarity	NPC187456
0.7718	Intermediate Similarity	NPC473547
0.7708	Intermediate Similarity	NPC473189
0.7701	Intermediate Similarity	NPC313791
0.767	Intermediate Similarity	NPC235900
0.767	Intermediate Similarity	NPC242556
0.7665	Intermediate Similarity	NPC195314
0.7647	Intermediate Similarity	NPC61637
0.7644	Intermediate Similarity	NPC314394
0.7641	Intermediate Similarity	NPC106833
0.7641	Intermediate Similarity	NPC469497
0.7638	Intermediate Similarity	NPC473747
0.7635	Intermediate Similarity	NPC476106
0.7632	Intermediate Similarity	NPC176199
0.7632	Intermediate Similarity	NPC215795
0.7632	Intermediate Similarity	NPC6093
0.7626	Intermediate Similarity	NPC231342
0.7619	Intermediate Similarity	NPC242446
0.7619	Intermediate Similarity	NPC475476
0.7617	Intermediate Similarity	NPC470873
0.7606	Intermediate Similarity	NPC313884
0.7606	Intermediate Similarity	NPC98371
0.76	Intermediate Similarity	NPC476175
0.7596	Intermediate Similarity	NPC471284
0.759	Intermediate Similarity	NPC128751
0.759	Intermediate Similarity	NPC246700
0.7588	Intermediate Similarity	NPC232130
0.7585	Intermediate Similarity	NPC48353
0.7579	Intermediate Similarity	NPC211997
0.7579	Intermediate Similarity	NPC151939
0.7579	Intermediate Similarity	NPC68354
0.7571	Intermediate Similarity	NPC469594
0.757	Intermediate Similarity	NPC475424
0.757	Intermediate Similarity	NPC79107
0.7568	Intermediate Similarity	NPC311276
0.7553	Intermediate Similarity	NPC470498
0.7548	Intermediate Similarity	NPC469592
0.7548	Intermediate Similarity	NPC471080
0.7546	Intermediate Similarity	NPC473806
0.7546	Intermediate Similarity	NPC471634
0.7536	Intermediate Similarity	NPC208284
0.7535	Intermediate Similarity	NPC249342
0.7526	Intermediate Similarity	NPC134586
0.7513	Intermediate Similarity	NPC97525
0.7512	Intermediate Similarity	NPC282033
0.7512	Intermediate Similarity	NPC193777
0.75	Intermediate Similarity	NPC300688
0.75	Intermediate Similarity	NPC229332
0.7488	Intermediate Similarity	NPC475422
0.7488	Intermediate Similarity	NPC291535
0.7488	Intermediate Similarity	NPC475112
0.7488	Intermediate Similarity	NPC475085
0.7487	Intermediate Similarity	NPC181502
0.7487	Intermediate Similarity	NPC85066
0.7487	Intermediate Similarity	NPC133366
0.7476	Intermediate Similarity	NPC127677
0.7474	Intermediate Similarity	NPC37423
0.7474	Intermediate Similarity	NPC329688
0.7474	Intermediate Similarity	NPC275305
0.7474	Intermediate Similarity	NPC189812
0.7473	Intermediate Similarity	NPC40779
0.7473	Intermediate Similarity	NPC271734
0.7464	Intermediate Similarity	NPC478074
0.7461	Intermediate Similarity	NPC302191
0.7459	Intermediate Similarity	NPC33421
0.7447	Intermediate Similarity	NPC317430
0.7447	Intermediate Similarity	NPC201700
0.7444	Intermediate Similarity	NPC470843
0.7444	Intermediate Similarity	NPC94541
0.7437	Intermediate Similarity	NPC474177
0.7427	Intermediate Similarity	NPC474905
0.7427	Intermediate Similarity	NPC46225
0.7423	Intermediate Similarity	NPC139291
0.7423	Intermediate Similarity	NPC472108
0.7423	Intermediate Similarity	NPC176127
0.7416	Intermediate Similarity	NPC475778
0.7413	Intermediate Similarity	NPC153042
0.7413	Intermediate Similarity	NPC70956
0.7413	Intermediate Similarity	NPC243834
0.7407	Intermediate Similarity	NPC194411
0.7404	Intermediate Similarity	NPC234999
0.7404	Intermediate Similarity	NPC126066
0.7394	Intermediate Similarity	NPC474561
0.7394	Intermediate Similarity	NPC49954
0.7391	Intermediate Similarity	NPC87755
0.7391	Intermediate Similarity	NPC475910
0.738	Intermediate Similarity	NPC102423
0.738	Intermediate Similarity	NPC194640
0.7376	Intermediate Similarity	NPC72211
0.7374	Intermediate Similarity	NPC206967
0.7368	Intermediate Similarity	NPC158129
0.7366	Intermediate Similarity	NPC131718
0.7358	Intermediate Similarity	NPC314552
0.7358	Intermediate Similarity	NPC88363
0.7358	Intermediate Similarity	NPC72980
0.7356	Intermediate Similarity	NPC477548
0.7356	Intermediate Similarity	NPC201697
0.7354	Intermediate Similarity	NPC63751
0.7352	Intermediate Similarity	NPC477531
0.7349	Intermediate Similarity	NPC469312
0.7349	Intermediate Similarity	NPC41318
0.7344	Intermediate Similarity	NPC56618
0.734	Intermediate Similarity	NPC128823
0.7339	Intermediate Similarity	NPC252251
0.7333	Intermediate Similarity	NPC473180
0.7326	Intermediate Similarity	NPC282231
0.7313	Intermediate Similarity	NPC43787
0.7313	Intermediate Similarity	NPC205934
0.7308	Intermediate Similarity	NPC258062
0.7308	Intermediate Similarity	NPC314957
0.7306	Intermediate Similarity	NPC209174
0.7304	Intermediate Similarity	NPC249040
0.7304	Intermediate Similarity	NPC329793
0.7302	Intermediate Similarity	NPC160105
0.7302	Intermediate Similarity	NPC477532
0.7302	Intermediate Similarity	NPC54988
0.7296	Intermediate Similarity	NPC190007
0.7296	Intermediate Similarity	NPC284678
0.7296	Intermediate Similarity	NPC472294
0.7296	Intermediate Similarity	NPC84478
0.7295	Intermediate Similarity	NPC18661
0.7291	Intermediate Similarity	NPC470499
0.7291	Intermediate Similarity	NPC265576
0.7287	Intermediate Similarity	NPC476118
0.7282	Intermediate Similarity	NPC98715
0.7282	Intermediate Similarity	NPC162484
0.7282	Intermediate Similarity	NPC476115
0.7277	Intermediate Similarity	NPC70259
0.7277	Intermediate Similarity	NPC312645
0.7273	Intermediate Similarity	NPC317030
0.7273	Intermediate Similarity	NPC279918
0.7269	Intermediate Similarity	NPC280272
0.7268	Intermediate Similarity	NPC133261
0.7268	Intermediate Similarity	NPC300183
0.7268	Intermediate Similarity	NPC267423
0.726	Intermediate Similarity	NPC225821
0.7259	Intermediate Similarity	NPC188387
0.7259	Intermediate Similarity	NPC163421
0.7259	Intermediate Similarity	NPC62510
0.7259	Intermediate Similarity	NPC94943
0.7258	Intermediate Similarity	NPC299594
0.7258	Intermediate Similarity	NPC469762
0.7256	Intermediate Similarity	NPC132642
0.7251	Intermediate Similarity	NPC151976
0.7251	Intermediate Similarity	NPC294620
0.7245	Intermediate Similarity	NPC48938
0.7244	Intermediate Similarity	NPC475844
0.724	Intermediate Similarity	NPC472123
0.7238	Intermediate Similarity	NPC199667
0.7237	Intermediate Similarity	NPC107836
0.7236	Intermediate Similarity	NPC65215
0.7236	Intermediate Similarity	NPC173028

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 NPC32200 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	562
0.2-0.3	766
0.3-0.4	1424
0.4-0.5	2969
0.5-0.6	2473
0.6-0.7	677
0.7-0.8	90
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
0.7978	Intermediate Similarity	NPD1325	Approved
0.7978	Intermediate Similarity	NPD1326	Approved
0.7814	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5913	Phase 3
0.7784	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD2382	Approved
0.7713	Intermediate Similarity	NPD2381	Approved
0.7713	Intermediate Similarity	NPD2380	Approved
0.7711	Intermediate Similarity	NPD2920	Discontinued
0.7696	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD5596	Phase 2
0.7632	Intermediate Similarity	NPD4076	Approved
0.7632	Intermediate Similarity	NPD4079	Approved
0.7617	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD6978	Phase 2
0.7612	Intermediate Similarity	NPD4511	Phase 1
0.7606	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD5003	Discontinued
0.7579	Intermediate Similarity	NPD3506	Approved
0.7579	Intermediate Similarity	NPD3505	Approved
0.7551	Intermediate Similarity	NPD2564	Approved
0.7551	Intermediate Similarity	NPD2565	Phase 2
0.7551	Intermediate Similarity	NPD6281	Approved
0.7549	Intermediate Similarity	NPD3003	Approved
0.7474	Intermediate Similarity	NPD5065	Approved
0.7463	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6455	Phase 3
0.7449	Intermediate Similarity	NPD8431	Approved
0.7426	Intermediate Similarity	NPD1768	Approved
0.7424	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6158	Phase 2
0.7418	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD5612	Discontinued
0.7368	Intermediate Similarity	NPD5936	Approved
0.7368	Intermediate Similarity	NPD5939	Approved
0.7363	Intermediate Similarity	NPD4462	Approved
0.7363	Intermediate Similarity	NPD4463	Approved
0.7358	Intermediate Similarity	NPD8386	Phase 2
0.7358	Intermediate Similarity	NPD5164	Discontinued
0.7356	Intermediate Similarity	NPD5834	Phase 3
0.7356	Intermediate Similarity	NPD5835	Phase 3
0.7354	Intermediate Similarity	NPD5021	Discontinued
0.7351	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5902	Approved
0.7346	Intermediate Similarity	NPD5903	Approved
0.734	Intermediate Similarity	NPD6249	Phase 2
0.734	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6248	Phase 2
0.733	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD2144	Approved
0.7295	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5138	Approved
0.7287	Intermediate Similarity	NPD5140	Approved
0.7286	Intermediate Similarity	NPD6220	Phase 3
0.7286	Intermediate Similarity	NPD4502	Phase 2
0.7278	Intermediate Similarity	NPD5254	Discontinued
0.7269	Intermediate Similarity	NPD6995	Phase 1
0.7264	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1592	Phase 3
0.7263	Intermediate Similarity	NPD4638	Approved
0.7263	Intermediate Similarity	NPD4640	Approved
0.7263	Intermediate Similarity	NPD4639	Approved
0.7255	Intermediate Similarity	NPD2175	Phase 3
0.7255	Intermediate Similarity	NPD2177	Approved
0.7255	Intermediate Similarity	NPD2176	Approved
0.7251	Intermediate Similarity	NPD3330	Phase 1
0.7241	Intermediate Similarity	NPD7948	Phase 1
0.7231	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD2882	Phase 1
0.7222	Intermediate Similarity	NPD5507	Approved
0.7222	Intermediate Similarity	NPD5506	Approved
0.7204	Intermediate Similarity	NPD5067	Phase 2
0.7204	Intermediate Similarity	NPD5066	Phase 2
0.72	Intermediate Similarity	NPD4499	Approved
0.7194	Intermediate Similarity	NPD3038	Discontinued
0.7186	Intermediate Similarity	NPD2383	Phase 1
0.7178	Intermediate Similarity	NPD1038	Approved
0.7178	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD1392	Approved
0.7172	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD8093	Discontinued
0.7165	Intermediate Similarity	NPD5100	Phase 3
0.7157	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7194	Discontinued
0.713	Intermediate Similarity	NPD7558	Phase 2
0.7123	Intermediate Similarity	NPD7470	Discontinued
0.7115	Intermediate Similarity	NPD5487	Phase 1
0.7113	Intermediate Similarity	NPD6492	Phase 2
0.7107	Intermediate Similarity	NPD4203	Approved
0.7107	Intermediate Similarity	NPD4204	Approved
0.7103	Intermediate Similarity	NPD4897	Phase 2
0.71	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6290	Phase 2
0.7087	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6985	Discontinued
0.7083	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5901	Discontinued
0.7079	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2510	Approved
0.7062	Intermediate Similarity	NPD5658	Approved
0.7062	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2509	Approved
0.7056	Intermediate Similarity	NPD8094	Discontinued
0.7041	Intermediate Similarity	NPD6159	Phase 2
0.704	Intermediate Similarity	NPD7688	Phase 1
0.7035	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3525	Discontinued
0.7026	Intermediate Similarity	NPD4128	Approved
0.7019	Intermediate Similarity	NPD6145	Phase 1
0.7014	Intermediate Similarity	NPD7222	Phase 2
0.7	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6206	Phase 1
0.6985	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2581	Approved
0.6984	Remote Similarity	NPD2582	Approved
0.698	Remote Similarity	NPD4334	Discontinued
0.6979	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3402	Phase 1
0.6971	Remote Similarity	NPD4600	Approved
0.6971	Remote Similarity	NPD4601	Approved
0.697	Remote Similarity	NPD6595	Phase 3
0.6967	Remote Similarity	NPD5530	Phase 1
0.6961	Remote Similarity	NPD3404	Approved
0.6957	Remote Similarity	NPD6261	Phase 3
0.6954	Remote Similarity	NPD4181	Approved
0.6954	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5255	Approved
0.6942	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3100	Discontinued
0.6934	Remote Similarity	NPD7452	Approved
0.6934	Remote Similarity	NPD7453	Approved
0.6931	Remote Similarity	NPD3390	Phase 2
0.6931	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3961	Discontinued
0.693	Remote Similarity	NPD7455	Approved
0.693	Remote Similarity	NPD7454	Approved
0.6927	Remote Similarity	NPD3323	Discontinued
0.6923	Remote Similarity	NPD3825	Phase 3
0.6915	Remote Similarity	NPD5075	Discontinued
0.6915	Remote Similarity	NPD6227	Discontinued
0.6912	Remote Similarity	NPD3389	Approved
0.6912	Remote Similarity	NPD3393	Approved
0.6912	Remote Similarity	NPD3394	Approved
0.6907	Remote Similarity	NPD2844	Phase 3
0.6904	Remote Similarity	NPD4075	Phase 2
0.6904	Remote Similarity	NPD5104	Approved
0.6898	Remote Similarity	NPD3835	Phase 3
0.6898	Remote Similarity	NPD3795	Approved
0.6898	Remote Similarity	NPD3794	Approved
0.6898	Remote Similarity	NPD3833	Phase 3
0.6893	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7957	Phase 1
0.6887	Remote Similarity	NPD7010	Phase 3
0.6887	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1685	Approved
0.6875	Remote Similarity	NPD1684	Approved
0.6875	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8364	Approved
0.6872	Remote Similarity	NPD8363	Approved
0.6872	Remote Similarity	NPD6176	Phase 1
0.6872	Remote Similarity	NPD7474	Suspended
0.6869	Remote Similarity	NPD8123	Approved
0.6869	Remote Similarity	NPD8122	Approved
0.6863	Remote Similarity	NPD5117	Phase 2
0.6858	Remote Similarity	NPD7796	Approved
0.6858	Remote Similarity	NPD7797	Approved
0.6853	Remote Similarity	NPD7921	Approved
0.6852	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7867	Phase 1
0.6849	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4951	Discontinued
0.6842	Remote Similarity	NPD8467	Approved
0.6842	Remote Similarity	NPD8466	Approved
0.6842	Remote Similarity	NPD8465	Approved
0.684	Remote Similarity	NPD4038	Approved
0.684	Remote Similarity	NPD4037	Approved
0.684	Remote Similarity	NPD4122	Approved
0.684	Remote Similarity	NPD31	Approved
0.684	Remote Similarity	NPD4039	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