NPASS Compound

Structure

NPC471458 OpenBabel07101718322D 26 28 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 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 0.8770 -1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1339 -2.3904 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 4.1835 0.1488 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 3.3175 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 1.5962 2.1100 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 2.9811 3.2315 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 1.6473 -0.5352 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 0.6691 -0.7431 0.0000 C 0 0 3 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 0.0000 0.0000 0.0000 N 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 2.3164 -1.2784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0740 -1.4123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 26 1 0 0 0 0 6 19 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 12 2 0 0 0 0 10 14 2 0 0 0 0 11 13 1 0 0 0 0 11 15 2 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 16 2 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 20 23 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.17
Volume:	367.076
LogP:	3.141
LogD:	2.898
LogS:	-3.525
# Rotatable Bonds:	5
TPSA:	83.55
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.811
Synthetic Accessibility Score:	4.028
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.725
MDCK Permeability:	2.6586178137222305e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.948
Plasma Protein Binding (PPB):	90.8369369506836%
Volume Distribution (VD):	0.729
Pgp-substrate:	3.463088035583496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.196
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.617
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.247
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.535
CYP3A4-inhibitor:	0.767
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	2.727
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.825
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.17
Carcinogencity:	0.113
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC471458

Natural Product ID:	NPC471458
*Common Name:**	Variecolorin H
IUPAC Name:	(6Z)-3-methoxy-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]piperazine-2,5-dione
Synonyms:	Variecolorin H
Standard InCHIKey:	AULFXBHXEZPTRY-PTNGSMBKSA-N
Standard InCHI:	InChI=1S/C20H23N3O3/c1-6-19(2,3)16-13(12-9-7-8-10-14(12)21-16)11-15-17(24)23-20(4,26-5)18(25)22-15/h6-11,21H,1H2,2-5H3,(H,22,25)(H,23,24)/b15-11-
SMILES:	CC1(C(=O)NC(=CC2=C(NC3=CC=CC=C32)C(C)(C)C=C)C(=O)N1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251052
PubChem CID:	23655530
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[570022]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[570022]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000.0	nM	PMID[570022]
NPT35	Others	n.a.		IC50	=	99000.0	nM	PMID[570022]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[570022]

☑ 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 NPC471458 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	297
0.1-0.2	2750
0.2-0.3	14613
0.3-0.4	17213
0.4-0.5	3851
0.5-0.6	2270
0.6-0.7	1337
0.7-0.8	329
0.8-0.85	23
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC473320
0.9441	High Similarity	NPC242556
0.9315	High Similarity	NPC37548
0.9195	High Similarity	NPC470507
0.9184	High Similarity	NPC124005
0.9067	High Similarity	NPC38736
0.9054	High Similarity	NPC187951
0.8919	High Similarity	NPC129042
0.8882	High Similarity	NPC184476
0.8824	High Similarity	NPC299594
0.8797	High Similarity	NPC470498
0.8642	High Similarity	NPC270009
0.8636	High Similarity	NPC285469
0.8625	High Similarity	NPC34508
0.8599	High Similarity	NPC271734
0.8562	High Similarity	NPC6982
0.8485	Intermediate Similarity	NPC472444
0.8481	Intermediate Similarity	NPC472587
0.8418	Intermediate Similarity	NPC16667
0.8415	Intermediate Similarity	NPC472443
0.8405	Intermediate Similarity	NPC288785
0.8397	Intermediate Similarity	NPC141353
0.8345	Intermediate Similarity	NPC22079
0.8343	Intermediate Similarity	NPC46413
0.8333	Intermediate Similarity	NPC207726
0.8313	Intermediate Similarity	NPC192270
0.8258	Intermediate Similarity	NPC105818
0.8258	Intermediate Similarity	NPC24678
0.8242	Intermediate Similarity	NPC293472
0.8176	Intermediate Similarity	NPC67056
0.8163	Intermediate Similarity	NPC475450
0.816	Intermediate Similarity	NPC280548
0.8121	Intermediate Similarity	NPC472586
0.8117	Intermediate Similarity	NPC314372
0.8117	Intermediate Similarity	NPC159856
0.8092	Intermediate Similarity	NPC2949
0.8086	Intermediate Similarity	NPC470508
0.8069	Intermediate Similarity	NPC250361
0.8042	Intermediate Similarity	NPC41174
0.8037	Intermediate Similarity	NPC470509
0.8037	Intermediate Similarity	NPC474561
0.8037	Intermediate Similarity	NPC49954
0.8027	Intermediate Similarity	NPC473587
0.8025	Intermediate Similarity	NPC311276
0.8025	Intermediate Similarity	NPC40779
0.8023	Intermediate Similarity	NPC34271
0.8023	Intermediate Similarity	NPC32200
0.7987	Intermediate Similarity	NPC190296
0.7973	Intermediate Similarity	NPC475428
0.7963	Intermediate Similarity	NPC282231
0.7959	Intermediate Similarity	NPC473762
0.795	Intermediate Similarity	NPC135141
0.795	Intermediate Similarity	NPC92796
0.7929	Intermediate Similarity	NPC198339
0.7925	Intermediate Similarity	NPC469760
0.7925	Intermediate Similarity	NPC469763
0.7925	Intermediate Similarity	NPC469765
0.7925	Intermediate Similarity	NPC469786
0.7925	Intermediate Similarity	NPC73952
0.7925	Intermediate Similarity	NPC25008
0.7925	Intermediate Similarity	NPC259644
0.7919	Intermediate Similarity	NPC179365
0.7901	Intermediate Similarity	NPC279918
0.7895	Intermediate Similarity	NPC165201
0.7888	Intermediate Similarity	NPC469762
0.7882	Intermediate Similarity	NPC314394
0.7881	Intermediate Similarity	NPC198988
0.7879	Intermediate Similarity	NPC63751
0.7879	Intermediate Similarity	NPC154293
0.7875	Intermediate Similarity	NPC80597
0.7875	Intermediate Similarity	NPC75540
0.7875	Intermediate Similarity	NPC212376
0.7875	Intermediate Similarity	NPC70922
0.7875	Intermediate Similarity	NPC211572
0.787	Intermediate Similarity	NPC176199
0.787	Intermediate Similarity	NPC215795
0.7867	Intermediate Similarity	NPC473930
0.7857	Intermediate Similarity	NPC59084
0.7829	Intermediate Similarity	NPC325252
0.7826	Intermediate Similarity	NPC469785
0.7818	Intermediate Similarity	NPC54988
0.7811	Intermediate Similarity	NPC68354
0.7806	Intermediate Similarity	NPC63157
0.7806	Intermediate Similarity	NPC473868
0.7805	Intermediate Similarity	NPC194640
0.7792	Intermediate Similarity	NPC104483
0.7785	Intermediate Similarity	NPC477134
0.7771	Intermediate Similarity	NPC201700
0.7771	Intermediate Similarity	NPC470440
0.7759	Intermediate Similarity	NPC119700
0.7746	Intermediate Similarity	NPC476319
0.7742	Intermediate Similarity	NPC469767
0.7742	Intermediate Similarity	NPC469783
0.7742	Intermediate Similarity	NPC469779
0.7742	Intermediate Similarity	NPC469761
0.7742	Intermediate Similarity	NPC469784
0.7742	Intermediate Similarity	NPC469780
0.7742	Intermediate Similarity	NPC469768
0.7738	Intermediate Similarity	NPC97525
0.7725	Intermediate Similarity	NPC194411
0.7712	Intermediate Similarity	NPC218268
0.7711	Intermediate Similarity	NPC160105
0.7706	Intermediate Similarity	NPC248454
0.7697	Intermediate Similarity	NPC8104
0.7692	Intermediate Similarity	NPC37423
0.7692	Intermediate Similarity	NPC469766
0.7692	Intermediate Similarity	NPC275305
0.7688	Intermediate Similarity	NPC33421
0.7683	Intermediate Similarity	NPC131718
0.7677	Intermediate Similarity	NPC73767
0.7677	Intermediate Similarity	NPC88097
0.7673	Intermediate Similarity	NPC471957
0.7667	Intermediate Similarity	NPC470499
0.7662	Intermediate Similarity	NPC125746
0.7662	Intermediate Similarity	NPC84911
0.7661	Intermediate Similarity	NPC72980
0.763	Intermediate Similarity	NPC163055
0.7628	Intermediate Similarity	NPC115611
0.7625	Intermediate Similarity	NPC2272
0.7616	Intermediate Similarity	NPC91179
0.7605	Intermediate Similarity	NPC49217
0.7605	Intermediate Similarity	NPC109447
0.7602	Intermediate Similarity	NPC59269
0.7602	Intermediate Similarity	NPC151939
0.7597	Intermediate Similarity	NPC96102
0.7597	Intermediate Similarity	NPC261195
0.7597	Intermediate Similarity	NPC29886
0.759	Intermediate Similarity	NPC476118
0.759	Intermediate Similarity	NPC102423
0.7588	Intermediate Similarity	NPC329688
0.7588	Intermediate Similarity	NPC189812
0.7574	Intermediate Similarity	NPC158129
0.7572	Intermediate Similarity	NPC302191
0.7571	Intermediate Similarity	NPC206967
0.7564	Intermediate Similarity	NPC110126
0.7564	Intermediate Similarity	NPC312092
0.7562	Intermediate Similarity	NPC21605
0.756	Intermediate Similarity	NPC317430
0.7558	Intermediate Similarity	NPC6093
0.7558	Intermediate Similarity	NPC11126
0.7556	Intermediate Similarity	NPC205403
0.7548	Intermediate Similarity	NPC105127
0.7543	Intermediate Similarity	NPC188387
0.7543	Intermediate Similarity	NPC280290
0.7543	Intermediate Similarity	NPC163421
0.7529	Intermediate Similarity	NPC472123
0.7529	Intermediate Similarity	NPC472108
0.7529	Intermediate Similarity	NPC313791
0.7529	Intermediate Similarity	NPC314603
0.7529	Intermediate Similarity	NPC19679
0.7529	Intermediate Similarity	NPC139291
0.7514	Intermediate Similarity	NPC300688
0.7514	Intermediate Similarity	NPC232130
0.75	Intermediate Similarity	NPC123019
0.75	Intermediate Similarity	NPC143872
0.7486	Intermediate Similarity	NPC228835
0.7485	Intermediate Similarity	NPC21174
0.7485	Intermediate Similarity	NPC271797
0.7469	Intermediate Similarity	NPC148592
0.7469	Intermediate Similarity	NPC53947
0.7459	Intermediate Similarity	NPC231342
0.7457	Intermediate Similarity	NPC213468
0.7455	Intermediate Similarity	NPC286427
0.7448	Intermediate Similarity	NPC81561
0.7442	Intermediate Similarity	NPC134586
0.7438	Intermediate Similarity	NPC204141
0.7429	Intermediate Similarity	NPC48938
0.7427	Intermediate Similarity	NPC474409
0.7425	Intermediate Similarity	NPC214106
0.7423	Intermediate Similarity	NPC216713
0.7421	Intermediate Similarity	NPC20144
0.7416	Intermediate Similarity	NPC221873
0.741	Intermediate Similarity	NPC206819
0.741	Intermediate Similarity	NPC475990
0.741	Intermediate Similarity	NPC230869
0.741	Intermediate Similarity	NPC318065
0.741	Intermediate Similarity	NPC41257
0.7405	Intermediate Similarity	NPC284635
0.7405	Intermediate Similarity	NPC279081
0.7403	Intermediate Similarity	NPC133366
0.7399	Intermediate Similarity	NPC211997
0.7391	Intermediate Similarity	NPC288838
0.7389	Intermediate Similarity	NPC477166
0.7389	Intermediate Similarity	NPC304187
0.7386	Intermediate Similarity	NPC190007
0.7379	Intermediate Similarity	NPC148140
0.7378	Intermediate Similarity	NPC200214
0.7371	Intermediate Similarity	NPC233936
0.7366	Intermediate Similarity	NPC476115
0.736	Intermediate Similarity	NPC317030
0.7358	Intermediate Similarity	NPC277157
0.7356	Intermediate Similarity	NPC88363
0.7356	Intermediate Similarity	NPC133261
0.7354	Intermediate Similarity	NPC477548
0.7348	Intermediate Similarity	NPC474177
0.7346	Intermediate Similarity	NPC179787
0.7346	Intermediate Similarity	NPC201380
0.7345	Intermediate Similarity	NPC94943
0.7338	Intermediate Similarity	NPC82295
0.733	Intermediate Similarity	NPC176127

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 NPC471458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	656
0.2-0.3	875
0.3-0.4	1585
0.4-0.5	2993
0.5-0.6	2261
0.6-0.7	516
0.7-0.8	80
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8497	Intermediate Similarity	NPD4463	Approved
0.8497	Intermediate Similarity	NPD4462	Approved
0.8141	Intermediate Similarity	NPD3835	Phase 3
0.8141	Intermediate Similarity	NPD3833	Phase 3
0.8039	Intermediate Similarity	NPD1592	Phase 3
0.7988	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3505	Approved
0.7811	Intermediate Similarity	NPD3506	Approved
0.7806	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4076	Approved
0.7765	Intermediate Similarity	NPD4079	Approved
0.7736	Intermediate Similarity	NPD3100	Discontinued
0.7725	Intermediate Similarity	NPD1325	Approved
0.7725	Intermediate Similarity	NPD1326	Approved
0.7707	Intermediate Similarity	NPD5254	Discontinued
0.7677	Intermediate Similarity	NPD786	Approved
0.7662	Intermediate Similarity	NPD1262	Discovery
0.7625	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5140	Approved
0.759	Intermediate Similarity	NPD5138	Approved
0.7588	Intermediate Similarity	NPD5065	Approved
0.758	Intermediate Similarity	NPD1722	Approved
0.7578	Intermediate Similarity	NPD2172	Phase 1
0.756	Intermediate Similarity	NPD5021	Discontinued
0.7529	Intermediate Similarity	NPD5596	Phase 2
0.7529	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6595	Phase 3
0.75	Intermediate Similarity	NPD2144	Approved
0.7458	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8386	Phase 2
0.7456	Intermediate Similarity	NPD2844	Phase 3
0.744	Intermediate Similarity	NPD2915	Discontinued
0.7434	Intermediate Similarity	NPD3654	Approved
0.7432	Intermediate Similarity	NPD6249	Phase 2
0.7432	Intermediate Similarity	NPD6248	Phase 2
0.7425	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4128	Approved
0.7371	Intermediate Similarity	NPD3038	Discontinued
0.7358	Intermediate Similarity	NPD5020	Approved
0.7355	Intermediate Similarity	NPD3385	Approved
0.7353	Intermediate Similarity	NPD4638	Approved
0.7353	Intermediate Similarity	NPD4640	Approved
0.7353	Intermediate Similarity	NPD4639	Approved
0.7349	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5104	Approved
0.7322	Intermediate Similarity	NPD5003	Discontinued
0.7317	Intermediate Similarity	NPD6158	Phase 2
0.7317	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4499	Approved
0.7273	Intermediate Similarity	NPD2837	Discontinued
0.7273	Intermediate Similarity	NPD5487	Phase 1
0.7263	Intermediate Similarity	NPD3961	Discontinued
0.7253	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5075	Discontinued
0.7246	Intermediate Similarity	NPD4326	Phase 2
0.7243	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4075	Phase 2
0.7241	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2381	Approved
0.7241	Intermediate Similarity	NPD2380	Approved
0.7241	Intermediate Similarity	NPD2382	Approved
0.7238	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5913	Phase 3
0.7235	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2882	Phase 1
0.7197	Intermediate Similarity	NPD4880	Discontinued
0.7196	Intermediate Similarity	NPD3003	Approved
0.7184	Intermediate Similarity	NPD482	Approved
0.7182	Intermediate Similarity	NPD2564	Approved
0.7182	Intermediate Similarity	NPD2565	Phase 2
0.7178	Intermediate Similarity	NPD1683	Approved
0.7178	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8431	Approved
0.716	Intermediate Similarity	NPD1404	Approved
0.716	Intermediate Similarity	NPD1403	Approved
0.7151	Intermediate Similarity	NPD2640	Approved
0.7151	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2641	Approved
0.7143	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2094	Phase 2
0.7135	Intermediate Similarity	NPD7948	Phase 1
0.7135	Intermediate Similarity	NPD2092	Phase 2
0.7135	Intermediate Similarity	NPD6206	Phase 1
0.7135	Intermediate Similarity	NPD2095	Phase 2
0.7127	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7619	Phase 3
0.712	Intermediate Similarity	NPD7618	Phase 3
0.7102	Intermediate Similarity	NPD4181	Approved
0.7099	Intermediate Similarity	NPD3525	Discontinued
0.7097	Intermediate Similarity	NPD947	Approved
0.7097	Intermediate Similarity	NPD6261	Phase 3
0.7095	Intermediate Similarity	NPD2096	Phase 2
0.7095	Intermediate Similarity	NPD2091	Phase 2
0.7093	Intermediate Similarity	NPD2639	Approved
0.7093	Intermediate Similarity	NPD2642	Approved
0.7081	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3323	Discontinued
0.7074	Intermediate Similarity	NPD4511	Phase 1
0.7072	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1038	Approved
0.7059	Intermediate Similarity	NPD1768	Approved
0.7052	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5612	Discontinued
0.7033	Intermediate Similarity	NPD4334	Discontinued
0.7031	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4702	Approved
0.703	Intermediate Similarity	NPD4703	Approved
0.7027	Intermediate Similarity	NPD4602	Approved
0.7022	Intermediate Similarity	NPD5897	Approved
0.7022	Intermediate Similarity	NPD5899	Approved
0.7022	Intermediate Similarity	NPD5898	Approved
0.701	Intermediate Similarity	NPD5066	Phase 2
0.701	Intermediate Similarity	NPD5067	Phase 2
0.7006	Intermediate Similarity	NPD6159	Phase 2
0.7	Intermediate Similarity	NPD45	Approved
0.7	Intermediate Similarity	NPD6554	Approved
0.6994	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4047	Discontinued
0.6989	Remote Similarity	NPD6492	Phase 2
0.6978	Remote Similarity	NPD2383	Phase 1
0.6957	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1256	Approved
0.6937	Remote Similarity	NPD1255	Approved
0.6937	Remote Similarity	NPD1253	Approved
0.6937	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1254	Approved
0.6932	Remote Similarity	NPD750	Phase 2
0.6931	Remote Similarity	NPD4601	Approved
0.6931	Remote Similarity	NPD4600	Approved
0.6927	Remote Similarity	NPD6452	Discontinued
0.6927	Remote Similarity	NPD5473	Discontinued
0.6923	Remote Similarity	NPD5444	Phase 1
0.6923	Remote Similarity	NPD2591	Phase 2
0.6923	Remote Similarity	NPD6217	Discontinued
0.6919	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD680	Discontinued
0.6906	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5902	Approved
0.6904	Remote Similarity	NPD5903	Approved
0.6901	Remote Similarity	NPD5255	Approved
0.6899	Remote Similarity	NPD1251	Discontinued
0.6882	Remote Similarity	NPD2150	Discontinued
0.6878	Remote Similarity	NPD3814	Phase 1
0.6875	Remote Similarity	NPD3609	Approved
0.6875	Remote Similarity	NPD3610	Approved
0.6875	Remote Similarity	NPD5901	Discontinued
0.6872	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8073	Approved
0.6859	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5501	Discontinued
0.6851	Remote Similarity	NPD3319	Phase 1
0.6851	Remote Similarity	NPD3320	Approved
0.6851	Remote Similarity	NPD3318	Approved
0.6842	Remote Similarity	NPD4501	Approved
0.6842	Remote Similarity	NPD4500	Approved
0.6839	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7957	Phase 1
0.6839	Remote Similarity	NPD2720	Phase 1
0.6836	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD43	Approved
0.6836	Remote Similarity	NPD6182	Approved
0.6835	Remote Similarity	NPD3476	Approved
0.6835	Remote Similarity	NPD3475	Approved
0.6828	Remote Similarity	NPD4315	Phase 2
0.6828	Remote Similarity	NPD4615	Phase 2
0.6826	Remote Similarity	NPD1661	Suspended
0.6826	Remote Similarity	NPD4547	Phase 3
0.6823	Remote Similarity	NPD6176	Phase 1
0.6823	Remote Similarity	NPD8072	Approved
0.6823	Remote Similarity	NPD2920	Discontinued
0.6821	Remote Similarity	NPD2480	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1392	Approved
0.6796	Remote Similarity	NPD4399	Phase 2
0.6796	Remote Similarity	NPD4203	Approved
0.6796	Remote Similarity	NPD4204	Approved
0.6791	Remote Similarity	NPD802	Phase 2
0.6789	Remote Similarity	NPD8396	Approved
0.6789	Remote Similarity	NPD2176	Approved
0.6789	Remote Similarity	NPD8395	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