NPASS Compound

Structure

NPC473320 OpenBabel07101718182D 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 -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 -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 -5.0495 1.3512 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 -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 -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 -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 -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 8 2 0 0 0 0 2 15 1 0 0 0 0 3 15 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 31 1 0 0 0 0 8 24 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 14 20 2 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 21 2 0 0 0 0 19 26 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 23 27 2 0 0 0 0 23 30 1 0 0 0 0 25 28 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	421.24
Volume:	450.92
LogP:	5.246
LogD:	3.912
LogS:	-4.225
# Rotatable Bonds:	7
TPSA:	83.55
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.659
Synthetic Accessibility Score:	4.216
Fsp3:	0.4
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:	-4.717
MDCK Permeability:	1.821998921514023e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.069
20% Bioavailability (F20%):	0.871
30% Bioavailability (F30%):	0.136

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.369
Plasma Protein Binding (PPB):	96.44640350341797%
Volume Distribution (VD):	0.976
Pgp-substrate:	1.5157582759857178%

ADMET: Metabolism

CYP1A2-inhibitor:	0.688
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.896
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.773
CYP2C9-substrate:	0.857
CYP2D6-inhibitor:	0.48
CYP2D6-substrate:	0.623
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	3.176
Half-life (T1/2):	0.488

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.418
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.258
Skin Sensitization:	0.152
Carcinogencity:	0.314
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC473320

Natural Product ID:	NPC473320
*Common Name:**	Variecolorin I
IUPAC Name:	(6Z)-3-methoxy-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-5-(3-methylbut-2-enyl)-1H-indol-3-yl]methylidene]piperazine-2,5-dione
Synonyms:	Variecolorin I
Standard InCHIKey:	XXJNZGPUCVMTGE-ZHZULCJRSA-N
Standard InCHI:	InChI=1S/C25H31N3O3/c1-8-24(4,5)21-18(14-20-22(29)28-25(6,31-7)23(30)27-20)17-13-16(10-9-15(2)3)11-12-19(17)26-21/h8-9,11-14,26H,1,10H2,2-7H3,(H,27,30)(H,28,29)/b20-14-
SMILES:	C=CC(c1[nH]c2c(c1/C=C/1N=C(O)C(N=C1O)(C)OC)cc(cc2)CC=C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400171
PubChem CID:	23655739
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[493042]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[493042]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000.0	nM	PMID[493042]
NPT35	Others	n.a.		IC50	=	79000.0	nM	PMID[493042]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[493042]

☑ 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 NPC473320 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	324
0.1-0.2	2406
0.2-0.3	14967
0.3-0.4	17445
0.4-0.5	3713
0.5-0.6	2273
0.6-0.7	1277
0.7-0.8	260
0.8-0.85	14
0.85-0.9	14
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC471458
0.9456	High Similarity	NPC124005
0.9333	High Similarity	NPC38736
0.9189	High Similarity	NPC129042
0.9184	High Similarity	NPC242556
0.9145	High Similarity	NPC184476
0.9067	High Similarity	NPC187951
0.9067	High Similarity	NPC37548
0.8954	High Similarity	NPC470507
0.8889	High Similarity	NPC270009
0.8875	High Similarity	NPC34508
0.8854	High Similarity	NPC271734
0.8812	High Similarity	NPC6982
0.8734	High Similarity	NPC472587
0.8671	High Similarity	NPC16667
0.865	High Similarity	NPC288785
0.8599	High Similarity	NPC299594
0.858	High Similarity	NPC46413
0.858	High Similarity	NPC470498
0.8554	High Similarity	NPC192270
0.8503	High Similarity	NPC472444
0.8434	Intermediate Similarity	NPC472443
0.8428	Intermediate Similarity	NPC67056
0.8418	Intermediate Similarity	NPC285469
0.8405	Intermediate Similarity	NPC280548
0.8354	Intermediate Similarity	NPC207726
0.8333	Intermediate Similarity	NPC470508
0.8263	Intermediate Similarity	NPC293472
0.8249	Intermediate Similarity	NPC32200
0.8188	Intermediate Similarity	NPC475450
0.8188	Intermediate Similarity	NPC179365
0.8187	Intermediate Similarity	NPC141353
0.8144	Intermediate Similarity	NPC472586
0.8121	Intermediate Similarity	NPC22079
0.8054	Intermediate Similarity	NPC473587
0.805	Intermediate Similarity	NPC24678
0.805	Intermediate Similarity	NPC105818
0.8	Intermediate Similarity	NPC475428
0.7987	Intermediate Similarity	NPC473762
0.7943	Intermediate Similarity	NPC34271
0.7911	Intermediate Similarity	NPC314372
0.7911	Intermediate Similarity	NPC159856
0.7904	Intermediate Similarity	NPC154293
0.7895	Intermediate Similarity	NPC176199
0.7895	Intermediate Similarity	NPC215795
0.7895	Intermediate Similarity	NPC473930
0.7885	Intermediate Similarity	NPC2949
0.7852	Intermediate Similarity	NPC250361
0.7849	Intermediate Similarity	NPC198339
0.7844	Intermediate Similarity	NPC49954
0.7844	Intermediate Similarity	NPC470509
0.7844	Intermediate Similarity	NPC474561
0.7836	Intermediate Similarity	NPC68354
0.7831	Intermediate Similarity	NPC40779
0.7831	Intermediate Similarity	NPC311276
0.7831	Intermediate Similarity	NPC194640
0.7823	Intermediate Similarity	NPC41174
0.7816	Intermediate Similarity	NPC165201
0.7785	Intermediate Similarity	NPC190296
0.7771	Intermediate Similarity	NPC282231
0.7758	Intermediate Similarity	NPC92796
0.7758	Intermediate Similarity	NPC135141
0.7751	Intermediate Similarity	NPC194411
0.773	Intermediate Similarity	NPC259644
0.773	Intermediate Similarity	NPC25008
0.773	Intermediate Similarity	NPC469760
0.773	Intermediate Similarity	NPC469765
0.773	Intermediate Similarity	NPC469763
0.773	Intermediate Similarity	NPC73952
0.773	Intermediate Similarity	NPC469786
0.7719	Intermediate Similarity	NPC275305
0.7719	Intermediate Similarity	NPC37423
0.7716	Intermediate Similarity	NPC33421
0.7711	Intermediate Similarity	NPC279918
0.7702	Intermediate Similarity	NPC477134
0.7701	Intermediate Similarity	NPC314394
0.7697	Intermediate Similarity	NPC469762
0.7692	Intermediate Similarity	NPC201700
0.7692	Intermediate Similarity	NPC63751
0.7684	Intermediate Similarity	NPC119700
0.7683	Intermediate Similarity	NPC211572
0.7683	Intermediate Similarity	NPC80597
0.7683	Intermediate Similarity	NPC75540
0.7683	Intermediate Similarity	NPC212376
0.7683	Intermediate Similarity	NPC70922
0.7677	Intermediate Similarity	NPC198988
0.767	Intermediate Similarity	NPC476319
0.7661	Intermediate Similarity	NPC97525
0.7658	Intermediate Similarity	NPC59084
0.7636	Intermediate Similarity	NPC469785
0.7633	Intermediate Similarity	NPC54988
0.7628	Intermediate Similarity	NPC325252
0.7624	Intermediate Similarity	NPC133366
0.7616	Intermediate Similarity	NPC189812
0.7616	Intermediate Similarity	NPC329688
0.7614	Intermediate Similarity	NPC190007
0.761	Intermediate Similarity	NPC63157
0.761	Intermediate Similarity	NPC473868
0.7595	Intermediate Similarity	NPC312092
0.7595	Intermediate Similarity	NPC104483
0.7593	Intermediate Similarity	NPC21605
0.7586	Intermediate Similarity	NPC88363
0.7584	Intermediate Similarity	NPC317030
0.7578	Intermediate Similarity	NPC470440
0.7571	Intermediate Similarity	NPC94943
0.7569	Intermediate Similarity	NPC474177
0.7557	Intermediate Similarity	NPC19679
0.7547	Intermediate Similarity	NPC469767
0.7547	Intermediate Similarity	NPC469768
0.7547	Intermediate Similarity	NPC469779
0.7547	Intermediate Similarity	NPC469784
0.7547	Intermediate Similarity	NPC469761
0.7547	Intermediate Similarity	NPC469780
0.7547	Intermediate Similarity	NPC469783
0.7541	Intermediate Similarity	NPC232130
0.7529	Intermediate Similarity	NPC151939
0.7529	Intermediate Similarity	NPC160105
0.7529	Intermediate Similarity	NPC248454
0.7516	Intermediate Similarity	NPC218268
0.7515	Intermediate Similarity	NPC8104
0.75	Intermediate Similarity	NPC470499
0.75	Intermediate Similarity	NPC131718
0.75	Intermediate Similarity	NPC206967
0.75	Intermediate Similarity	NPC469766
0.75	Intermediate Similarity	NPC302191
0.7486	Intermediate Similarity	NPC205403
0.7486	Intermediate Similarity	NPC204565
0.7486	Intermediate Similarity	NPC72980
0.7486	Intermediate Similarity	NPC6093
0.7485	Intermediate Similarity	NPC76982
0.7485	Intermediate Similarity	NPC471957
0.7484	Intermediate Similarity	NPC88097
0.7484	Intermediate Similarity	NPC73767
0.7472	Intermediate Similarity	NPC473189
0.7468	Intermediate Similarity	NPC84911
0.7468	Intermediate Similarity	NPC125746
0.7458	Intermediate Similarity	NPC212535
0.7458	Intermediate Similarity	NPC163055
0.745	Intermediate Similarity	NPC215519
0.7446	Intermediate Similarity	NPC70956
0.7446	Intermediate Similarity	NPC243834
0.7444	Intermediate Similarity	NPC65215
0.7444	Intermediate Similarity	NPC246700
0.7444	Intermediate Similarity	NPC173028
0.7443	Intermediate Similarity	NPC300688
0.7443	Intermediate Similarity	NPC91179
0.744	Intermediate Similarity	NPC206819
0.744	Intermediate Similarity	NPC318065
0.7439	Intermediate Similarity	NPC2272
0.7438	Intermediate Similarity	NPC115611
0.7433	Intermediate Similarity	NPC123019
0.7429	Intermediate Similarity	NPC59269
0.7427	Intermediate Similarity	NPC49217
0.7427	Intermediate Similarity	NPC109447
0.7412	Intermediate Similarity	NPC476118
0.7412	Intermediate Similarity	NPC102423
0.7405	Intermediate Similarity	NPC29886
0.7405	Intermediate Similarity	NPC473747
0.7405	Intermediate Similarity	NPC261195
0.7405	Intermediate Similarity	NPC96102
0.7399	Intermediate Similarity	NPC158129
0.7391	Intermediate Similarity	NPC231342
0.7386	Intermediate Similarity	NPC213468
0.7386	Intermediate Similarity	NPC11126
0.7384	Intermediate Similarity	NPC317430
0.7381	Intermediate Similarity	NPC286427
0.7375	Intermediate Similarity	NPC110126
0.7374	Intermediate Similarity	NPC163421
0.7374	Intermediate Similarity	NPC188387
0.7374	Intermediate Similarity	NPC280290
0.7368	Intermediate Similarity	NPC122718
0.7366	Intermediate Similarity	NPC128823
0.736	Intermediate Similarity	NPC139291
0.736	Intermediate Similarity	NPC472108
0.7358	Intermediate Similarity	NPC105127
0.7356	Intermediate Similarity	NPC313791
0.7356	Intermediate Similarity	NPC472123
0.7356	Intermediate Similarity	NPC314603
0.7337	Intermediate Similarity	NPC181502
0.7337	Intermediate Similarity	NPC85066
0.7337	Intermediate Similarity	NPC41257
0.7333	Intermediate Similarity	NPC474707
0.7326	Intermediate Similarity	NPC475151
0.7318	Intermediate Similarity	NPC228835
0.7317	Intermediate Similarity	NPC143872
0.731	Intermediate Similarity	NPC21174
0.731	Intermediate Similarity	NPC271797
0.731	Intermediate Similarity	NPC90723
0.7296	Intermediate Similarity	NPC96131
0.7294	Intermediate Similarity	NPC44773
0.7294	Intermediate Similarity	NPC215584
0.7289	Intermediate Similarity	NPC53947
0.7289	Intermediate Similarity	NPC148592
0.7273	Intermediate Similarity	NPC134586
0.7267	Intermediate Similarity	NPC115232
0.7263	Intermediate Similarity	NPC48938
0.7258	Intermediate Similarity	NPC153042
0.7257	Intermediate Similarity	NPC474409
0.7256	Intermediate Similarity	NPC204141
0.7253	Intermediate Similarity	NPC242928

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 NPC473320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	646
0.2-0.3	897
0.3-0.4	1725
0.4-0.5	3001
0.5-0.6	2173
0.6-0.7	448
0.7-0.8	68
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
0.828	Intermediate Similarity	NPD4462	Approved
0.828	Intermediate Similarity	NPD4463	Approved
0.7987	Intermediate Similarity	NPD3100	Discontinued
0.7964	Intermediate Similarity	NPD1325	Approved
0.7964	Intermediate Similarity	NPD1326	Approved
0.7937	Intermediate Similarity	NPD3833	Phase 3
0.7937	Intermediate Similarity	NPD3835	Phase 3
0.7892	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD3506	Approved
0.7836	Intermediate Similarity	NPD3505	Approved
0.7834	Intermediate Similarity	NPD1592	Phase 3
0.7826	Intermediate Similarity	NPD2172	Phase 1
0.7798	Intermediate Similarity	NPD5021	Discontinued
0.7798	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4076	Approved
0.7791	Intermediate Similarity	NPD4079	Approved
0.7736	Intermediate Similarity	NPD5254	Discontinued
0.7733	Intermediate Similarity	NPD2144	Approved
0.7688	Intermediate Similarity	NPD8386	Phase 2
0.7658	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3038	Discontinued
0.7558	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD786	Approved
0.7468	Intermediate Similarity	NPD1262	Discovery
0.7442	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1683	Approved
0.7414	Intermediate Similarity	NPD5065	Approved
0.7414	Intermediate Similarity	NPD4128	Approved
0.7412	Intermediate Similarity	NPD5140	Approved
0.7412	Intermediate Similarity	NPD5138	Approved
0.7405	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1403	Approved
0.7396	Intermediate Similarity	NPD1404	Approved
0.7391	Intermediate Similarity	NPD1722	Approved
0.7384	Intermediate Similarity	NPD2641	Approved
0.7384	Intermediate Similarity	NPD2640	Approved
0.7384	Intermediate Similarity	NPD4640	Approved
0.7384	Intermediate Similarity	NPD4638	Approved
0.7384	Intermediate Similarity	NPD4639	Approved
0.7374	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5596	Phase 2
0.7353	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6595	Phase 3
0.7337	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2642	Approved
0.7326	Intermediate Similarity	NPD2639	Approved
0.7293	Intermediate Similarity	NPD3961	Discontinued
0.7293	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4511	Phase 1
0.7283	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2844	Phase 3
0.7273	Intermediate Similarity	NPD6248	Phase 2
0.7273	Intermediate Similarity	NPD4075	Phase 2
0.7273	Intermediate Similarity	NPD6249	Phase 2
0.7273	Intermediate Similarity	NPD2381	Approved
0.7273	Intermediate Similarity	NPD2380	Approved
0.7273	Intermediate Similarity	NPD2382	Approved
0.7267	Intermediate Similarity	NPD2915	Discontinued
0.7247	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2882	Phase 1
0.7244	Intermediate Similarity	NPD3654	Approved
0.7239	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD2564	Approved
0.7213	Intermediate Similarity	NPD2565	Phase 2
0.7213	Intermediate Similarity	NPD4499	Approved
0.7198	Intermediate Similarity	NPD8431	Approved
0.7178	Intermediate Similarity	NPD5020	Approved
0.7176	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5104	Approved
0.7174	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5913	Phase 3
0.717	Intermediate Similarity	NPD3385	Approved
0.7166	Intermediate Similarity	NPD5003	Discontinued
0.7143	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6158	Phase 2
0.7135	Intermediate Similarity	NPD4181	Approved
0.7134	Intermediate Similarity	NPD947	Approved
0.7127	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4880	Discontinued
0.712	Intermediate Similarity	NPD5487	Phase 1
0.7112	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3323	Discontinued
0.7104	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2837	Discontinued
0.7097	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5075	Discontinued
0.7083	Intermediate Similarity	NPD5901	Discontinued
0.7081	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4326	Phase 2
0.7072	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2720	Phase 1
0.7066	Intermediate Similarity	NPD4547	Phase 3
0.7047	Intermediate Similarity	NPD3003	Approved
0.7022	Intermediate Similarity	NPD482	Approved
0.7006	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7948	Phase 1
0.6984	Remote Similarity	NPD6206	Phase 1
0.6978	Remote Similarity	NPD5106	Approved
0.6978	Remote Similarity	NPD2094	Phase 2
0.6978	Remote Similarity	NPD2092	Phase 2
0.6978	Remote Similarity	NPD5105	Approved
0.6978	Remote Similarity	NPD2095	Phase 2
0.6975	Remote Similarity	NPD1255	Approved
0.6975	Remote Similarity	NPD1254	Approved
0.6975	Remote Similarity	NPD1253	Approved
0.6975	Remote Similarity	NPD1256	Approved
0.6974	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7618	Phase 3
0.6968	Remote Similarity	NPD7619	Phase 3
0.6961	Remote Similarity	NPD5473	Discontinued
0.6961	Remote Similarity	NPD702	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3404	Approved
0.6947	Remote Similarity	NPD6261	Phase 3
0.694	Remote Similarity	NPD2096	Phase 2
0.694	Remote Similarity	NPD2091	Phase 2
0.694	Remote Similarity	NPD4957	Phase 2
0.6939	Remote Similarity	NPD5835	Phase 3
0.6939	Remote Similarity	NPD5834	Phase 3
0.6937	Remote Similarity	NPD1251	Discontinued
0.6928	Remote Similarity	NPD3525	Discontinued
0.6919	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3330	Phase 1
0.6915	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD1038	Approved
0.6911	Remote Similarity	NPD1768	Approved
0.691	Remote Similarity	NPD3609	Approved
0.691	Remote Similarity	NPD3610	Approved
0.69	Remote Similarity	NPD5612	Discontinued
0.6882	Remote Similarity	NPD4334	Discontinued
0.6878	Remote Similarity	NPD4602	Approved
0.6875	Remote Similarity	NPD4601	Approved
0.6875	Remote Similarity	NPD4600	Approved
0.6872	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5066	Phase 2
0.6869	Remote Similarity	NPD5067	Phase 2
0.6868	Remote Similarity	NPD5898	Approved
0.6868	Remote Similarity	NPD5899	Approved
0.6868	Remote Similarity	NPD5897	Approved
0.6864	Remote Similarity	NPD4703	Approved
0.6864	Remote Similarity	NPD4702	Approved
0.6856	Remote Similarity	NPD2920	Discontinued
0.6851	Remote Similarity	NPD6159	Phase 2
0.6836	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6492	Phase 2
0.6829	Remote Similarity	NPD6554	Approved
0.6829	Remote Similarity	NPD45	Approved
0.6828	Remote Similarity	NPD2383	Phase 1
0.6826	Remote Similarity	NPD4047	Discontinued
0.6823	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2580	Discontinued
0.6802	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7957	Phase 1
0.6786	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD750	Phase 2
0.6776	Remote Similarity	NPD6452	Discontinued
0.6774	Remote Similarity	NPD2591	Phase 2
0.6774	Remote Similarity	NPD5444	Phase 1
0.6774	Remote Similarity	NPD6217	Discontinued
0.6768	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5903	Approved
0.6766	Remote Similarity	NPD5902	Approved
0.6761	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7454	Approved
0.675	Remote Similarity	NPD7455	Approved
0.6747	Remote Similarity	NPD680	Discontinued
0.6743	Remote Similarity	NPD5255	Approved
0.6736	Remote Similarity	NPD3814	Phase 1
0.6724	Remote Similarity	NPD2150	Discontinued
0.6721	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3417	Phase 1
0.672	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6664	Approved
0.6718	Remote Similarity	NPD8073	Approved
0.6703	Remote Similarity	NPD3318	Approved
0.6703	Remote Similarity	NPD5501	Discontinued
0.6703	Remote Similarity	NPD3320	Approved
0.6703	Remote Similarity	NPD3319	Phase 1
0.6703	Remote Similarity	NPD5100	Phase 3
0.6703	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4501	Approved
0.6701	Remote Similarity	NPD4500	Approved
0.67	Remote Similarity	NPD6220	Phase 3

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