NPASS Compound

Structure

NPC187951 OpenBabel07101718282D 29 31 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 -8.5136 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6476 3.1488 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 -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 -6.7816 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9156 2.1488 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 -7.6476 2.1488 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 -5.0495 1.6488 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 -1.2872 1.1590 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 -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 -1.9563 0.4158 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 -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 14 1 0 0 0 0 3 14 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 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 13 19 2 0 0 0 0 15 4 1 1 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 19 23 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 24 1 0 0 0 0 21 27 1 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 25 2 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	391.23
Volume:	424.833
LogP:	5.148
LogD:	3.953
LogS:	-3.274
# Rotatable Bonds:	6
TPSA:	81.77
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	3.49
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:	-5.108
MDCK Permeability:	1.5361034456873313e-05
Pgp-inhibitor:	0.706
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.049
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	99.4121322631836%
Volume Distribution (VD):	0.222
Pgp-substrate:	1.2298856973648071%

ADMET: Metabolism

CYP1A2-inhibitor:	0.487
CYP1A2-substrate:	0.818
CYP2C19-inhibitor:	0.772
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.814
CYP2D6-inhibitor:	0.891
CYP2D6-substrate:	0.487
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.77

ADMET: Excretion

Clearance (CL):	3.186
Half-life (T1/2):	0.602

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.843
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.76
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.13
Carcinogencity:	0.065
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC187951

Natural Product ID:	NPC187951
*Common Name:**	Variecolorin G
IUPAC Name:	(3S,6Z)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-7-(3-methylbut-2-enyl)-1H-indol-3-yl]methylidene]piperazine-2,5-dione
Synonyms:	Variecolorin G
Standard InCHIKey:	CVRBXJYAJQNPNW-CCNLRRDASA-N
Standard InCHI:	InChI=1S/C24H29N3O2/c1-7-24(5,6)21-18(13-19-23(29)25-15(4)22(28)26-19)17-10-8-9-16(20(17)27-21)12-11-14(2)3/h7-11,13,15,27H,1,12H2,2-6H3,(H,25,29)(H,26,28)/b19-13-/t15-/m0/s1
SMILES:	C=CC(C)(C)c1c(/C=C2/C(=N[C@@H](C)C(=N2)O)O)c2cccc(CC=C(C)C)c2[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251051
PubChem CID:	23655738
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]
NPO32843	eurotium cristatum en-220	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22727636]
NPO32640	eurotium rubrum ma-150	Species	Aspergillaceae	Eukaryota	Fungus Obtained from Marine Mangrove-Derived Rhizospheric Soil.	n.a.	n.a.	PMID[25730346]

☑ 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
LD50	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	2
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[564016]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[564016]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000.0	nM	PMID[564016]
NPT35	Others	n.a.		IC50	=	86000.0	nM	PMID[564016]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[564016]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	42.6	ug ml-1	PMID[564017]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	22.0	uM	PMID[564018]

☑ 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 NPC187951 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	410
0.1-0.2	3195
0.2-0.3	16943
0.3-0.4	14627
0.4-0.5	3581
0.5-0.6	2240
0.6-0.7	1310
0.7-0.8	337
0.8-0.85	29
0.85-0.9	14
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC38736
0.9716	High Similarity	NPC37548
0.9448	High Similarity	NPC470507
0.9441	High Similarity	NPC124005
0.9437	High Similarity	NPC129042
0.9433	High Similarity	NPC242556
0.9329	High Similarity	NPC472587
0.9184	High Similarity	NPC207726
0.9122	High Similarity	NPC184476
0.9067	High Similarity	NPC473320
0.9054	High Similarity	NPC471458
0.9026	High Similarity	NPC6982
0.9007	High Similarity	NPC16667
0.9	High Similarity	NPC67056
0.8993	High Similarity	NPC285469
0.8968	High Similarity	NPC34508
0.8854	High Similarity	NPC288785
0.8824	High Similarity	NPC271734
0.8808	High Similarity	NPC299594
0.8797	High Similarity	NPC293472
0.8766	High Similarity	NPC470508
0.8742	High Similarity	NPC270009
0.8742	High Similarity	NPC472443
0.8718	High Similarity	NPC280548
0.8634	High Similarity	NPC192270
0.8582	High Similarity	NPC22079
0.8581	High Similarity	NPC194640
0.858	High Similarity	NPC472444
0.8497	Intermediate Similarity	NPC141353
0.8477	Intermediate Similarity	NPC24678
0.8477	Intermediate Similarity	NPC105818
0.8438	Intermediate Similarity	NPC472586
0.8392	Intermediate Similarity	NPC475450
0.8354	Intermediate Similarity	NPC49954
0.8354	Intermediate Similarity	NPC474561
0.8333	Intermediate Similarity	NPC159856
0.8333	Intermediate Similarity	NPC314372
0.8323	Intermediate Similarity	NPC46413
0.8311	Intermediate Similarity	NPC2949
0.828	Intermediate Similarity	NPC282231
0.8252	Intermediate Similarity	NPC473587
0.8217	Intermediate Similarity	NPC279918
0.82	Intermediate Similarity	NPC190296
0.8199	Intermediate Similarity	NPC470498
0.8194	Intermediate Similarity	NPC475428
0.8187	Intermediate Similarity	NPC63751
0.8182	Intermediate Similarity	NPC473762
0.8171	Intermediate Similarity	NPC176199
0.8171	Intermediate Similarity	NPC215795
0.8163	Intermediate Similarity	NPC325252
0.8153	Intermediate Similarity	NPC92796
0.8153	Intermediate Similarity	NPC135141
0.8138	Intermediate Similarity	NPC179365
0.8137	Intermediate Similarity	NPC194411
0.8133	Intermediate Similarity	NPC473868
0.8133	Intermediate Similarity	NPC63157
0.8129	Intermediate Similarity	NPC25008
0.8129	Intermediate Similarity	NPC469763
0.8129	Intermediate Similarity	NPC469786
0.8129	Intermediate Similarity	NPC469760
0.8129	Intermediate Similarity	NPC259644
0.8129	Intermediate Similarity	NPC469765
0.8129	Intermediate Similarity	NPC73952
0.8117	Intermediate Similarity	NPC33421
0.811	Intermediate Similarity	NPC68354
0.8095	Intermediate Similarity	NPC198988
0.8082	Intermediate Similarity	NPC473930
0.8077	Intermediate Similarity	NPC212376
0.8077	Intermediate Similarity	NPC70922
0.8077	Intermediate Similarity	NPC75540
0.8077	Intermediate Similarity	NPC80597
0.8077	Intermediate Similarity	NPC211572
0.8067	Intermediate Similarity	NPC59084
0.8042	Intermediate Similarity	NPC250361
0.8041	Intermediate Similarity	NPC218268
0.8014	Intermediate Similarity	NPC41174
0.8012	Intermediate Similarity	NPC160105
0.8012	Intermediate Similarity	NPC54988
0.8	Intermediate Similarity	NPC88097
0.7988	Intermediate Similarity	NPC37423
0.7988	Intermediate Similarity	NPC275305
0.7987	Intermediate Similarity	NPC21605
0.7975	Intermediate Similarity	NPC469762
0.7974	Intermediate Similarity	NPC470440
0.7963	Intermediate Similarity	NPC201700
0.7947	Intermediate Similarity	NPC469768
0.7947	Intermediate Similarity	NPC469779
0.7947	Intermediate Similarity	NPC469784
0.7947	Intermediate Similarity	NPC469780
0.7947	Intermediate Similarity	NPC469783
0.7947	Intermediate Similarity	NPC469761
0.7947	Intermediate Similarity	NPC469767
0.7911	Intermediate Similarity	NPC469785
0.7904	Intermediate Similarity	NPC91179
0.7901	Intermediate Similarity	NPC109447
0.7898	Intermediate Similarity	NPC32200
0.7895	Intermediate Similarity	NPC469766
0.7892	Intermediate Similarity	NPC248454
0.7892	Intermediate Similarity	NPC59269
0.7888	Intermediate Similarity	NPC311276
0.7881	Intermediate Similarity	NPC73767
0.7881	Intermediate Similarity	NPC104483
0.7875	Intermediate Similarity	NPC131718
0.7871	Intermediate Similarity	NPC477134
0.7871	Intermediate Similarity	NPC471957
0.787	Intermediate Similarity	NPC165495
0.7867	Intermediate Similarity	NPC125746
0.7867	Intermediate Similarity	NPC84911
0.7844	Intermediate Similarity	NPC11126
0.7843	Intermediate Similarity	NPC20144
0.7829	Intermediate Similarity	NPC115611
0.7821	Intermediate Similarity	NPC2272
0.7818	Intermediate Similarity	NPC314603
0.7812	Intermediate Similarity	NPC206819
0.7812	Intermediate Similarity	NPC318065
0.7812	Intermediate Similarity	NPC41257
0.78	Intermediate Similarity	NPC96102
0.78	Intermediate Similarity	NPC29886
0.78	Intermediate Similarity	NPC261195
0.7798	Intermediate Similarity	NPC198339
0.7791	Intermediate Similarity	NPC49217
0.7791	Intermediate Similarity	NPC470509
0.7784	Intermediate Similarity	NPC232130
0.7778	Intermediate Similarity	NPC476118
0.7778	Intermediate Similarity	NPC40779
0.7771	Intermediate Similarity	NPC133366
0.7771	Intermediate Similarity	NPC189812
0.7771	Intermediate Similarity	NPC329688
0.7765	Intermediate Similarity	NPC228835
0.7763	Intermediate Similarity	NPC312092
0.7763	Intermediate Similarity	NPC110126
0.775	Intermediate Similarity	NPC286427
0.7748	Intermediate Similarity	NPC105127
0.7744	Intermediate Similarity	NPC317430
0.7744	Intermediate Similarity	NPC154293
0.7742	Intermediate Similarity	NPC204141
0.7738	Intermediate Similarity	NPC72980
0.7738	Intermediate Similarity	NPC213468
0.7733	Intermediate Similarity	NPC204565
0.7733	Intermediate Similarity	NPC317030
0.7719	Intermediate Similarity	NPC476319
0.7714	Intermediate Similarity	NPC474177
0.7711	Intermediate Similarity	NPC472123
0.7706	Intermediate Similarity	NPC19679
0.7706	Intermediate Similarity	NPC163055
0.7702	Intermediate Similarity	NPC475990
0.7692	Intermediate Similarity	NPC143872
0.7688	Intermediate Similarity	NPC65215
0.7688	Intermediate Similarity	NPC173028
0.7679	Intermediate Similarity	NPC151939
0.7669	Intermediate Similarity	NPC21174
0.7669	Intermediate Similarity	NPC102423
0.7669	Intermediate Similarity	NPC271797
0.7658	Intermediate Similarity	NPC53947
0.7658	Intermediate Similarity	NPC148592
0.7657	Intermediate Similarity	NPC477166
0.7657	Intermediate Similarity	NPC304187
0.7651	Intermediate Similarity	NPC158129
0.761	Intermediate Similarity	NPC216713
0.7605	Intermediate Similarity	NPC313791
0.7605	Intermediate Similarity	NPC97525
0.7597	Intermediate Similarity	NPC279081
0.7593	Intermediate Similarity	NPC56765
0.7588	Intermediate Similarity	NPC300688
0.758	Intermediate Similarity	NPC288838
0.7572	Intermediate Similarity	NPC474707
0.7562	Intermediate Similarity	NPC200214
0.7558	Intermediate Similarity	NPC472294
0.7544	Intermediate Similarity	NPC233936
0.7535	Intermediate Similarity	NPC81561
0.7533	Intermediate Similarity	NPC82295
0.7532	Intermediate Similarity	NPC201380
0.7532	Intermediate Similarity	NPC179787
0.7531	Intermediate Similarity	NPC129721
0.7529	Intermediate Similarity	NPC219336
0.7529	Intermediate Similarity	NPC17059
0.7515	Intermediate Similarity	NPC267885
0.7514	Intermediate Similarity	NPC280290
0.7514	Intermediate Similarity	NPC15102
0.75	Intermediate Similarity	NPC472108
0.75	Intermediate Similarity	NPC64055
0.75	Intermediate Similarity	NPC215519
0.75	Intermediate Similarity	NPC139291
0.75	Intermediate Similarity	NPC161861
0.7486	Intermediate Similarity	NPC34271
0.7485	Intermediate Similarity	NPC474880
0.7485	Intermediate Similarity	NPC230869
0.7485	Intermediate Similarity	NPC221786
0.7484	Intermediate Similarity	NPC238499
0.7484	Intermediate Similarity	NPC321911
0.7484	Intermediate Similarity	NPC230002
0.7471	Intermediate Similarity	NPC217372
0.7471	Intermediate Similarity	NPC15573
0.7471	Intermediate Similarity	NPC94752
0.7471	Intermediate Similarity	NPC326575
0.7471	Intermediate Similarity	NPC183662
0.7469	Intermediate Similarity	NPC51054
0.7468	Intermediate Similarity	NPC63545
0.7465	Intermediate Similarity	NPC148140
0.7457	Intermediate Similarity	NPC190007

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 NPC187951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	578
0.2-0.3	980
0.3-0.4	1541
0.4-0.5	2921
0.5-0.6	2180
0.6-0.7	609
0.7-0.8	108
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8725	High Similarity	NPD4462	Approved
0.8725	High Similarity	NPD4463	Approved
0.8291	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD1325	Approved
0.825	Intermediate Similarity	NPD1326	Approved
0.817	Intermediate Similarity	NPD3100	Discontinued
0.8146	Intermediate Similarity	NPD5254	Discontinued
0.811	Intermediate Similarity	NPD3506	Approved
0.811	Intermediate Similarity	NPD3505	Approved
0.8075	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD8386	Phase 2
0.8061	Intermediate Similarity	NPD4079	Approved
0.8061	Intermediate Similarity	NPD4076	Approved
0.8013	Intermediate Similarity	NPD1592	Phase 3
0.8	Intermediate Similarity	NPD2172	Phase 1
0.8	Intermediate Similarity	NPD786	Approved
0.7927	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5065	Approved
0.7853	Intermediate Similarity	NPD5021	Discontinued
0.7821	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD2144	Approved
0.7784	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1722	Approved
0.7778	Intermediate Similarity	NPD5138	Approved
0.7778	Intermediate Similarity	NPD5140	Approved
0.7771	Intermediate Similarity	NPD4128	Approved
0.7771	Intermediate Similarity	NPD3835	Phase 3
0.7771	Intermediate Similarity	NPD3833	Phase 3
0.7755	Intermediate Similarity	NPD3654	Approved
0.7744	Intermediate Similarity	NPD4640	Approved
0.7744	Intermediate Similarity	NPD4639	Approved
0.7744	Intermediate Similarity	NPD4638	Approved
0.7727	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6158	Phase 2
0.7722	Intermediate Similarity	NPD2882	Phase 1
0.7692	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1683	Approved
0.7692	Intermediate Similarity	NPD6595	Phase 3
0.7667	Intermediate Similarity	NPD3385	Approved
0.7662	Intermediate Similarity	NPD5020	Approved
0.7647	Intermediate Similarity	NPD3038	Discontinued
0.7632	Intermediate Similarity	NPD1262	Discovery
0.763	Intermediate Similarity	NPD3961	Discontinued
0.763	Intermediate Similarity	NPD8431	Approved
0.7622	Intermediate Similarity	NPD2915	Discontinued
0.7619	Intermediate Similarity	NPD4075	Phase 2
0.7616	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1404	Approved
0.7546	Intermediate Similarity	NPD1403	Approved
0.7531	Intermediate Similarity	NPD4326	Phase 2
0.753	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2640	Approved
0.753	Intermediate Similarity	NPD2641	Approved
0.7529	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2381	Approved
0.7515	Intermediate Similarity	NPD2380	Approved
0.7515	Intermediate Similarity	NPD2382	Approved
0.7515	Intermediate Similarity	NPD5104	Approved
0.75	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4880	Discontinued
0.75	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4181	Approved
0.747	Intermediate Similarity	NPD2639	Approved
0.747	Intermediate Similarity	NPD2642	Approved
0.7456	Intermediate Similarity	NPD482	Approved
0.7455	Intermediate Similarity	NPD3323	Discontinued
0.7453	Intermediate Similarity	NPD2837	Discontinued
0.7443	Intermediate Similarity	NPD4499	Approved
0.7436	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2844	Phase 3
0.7423	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4703	Approved
0.7421	Intermediate Similarity	NPD4702	Approved
0.7412	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5596	Phase 2
0.7399	Intermediate Similarity	NPD2092	Phase 2
0.7399	Intermediate Similarity	NPD2094	Phase 2
0.7399	Intermediate Similarity	NPD2095	Phase 2
0.7389	Intermediate Similarity	NPD4047	Discontinued
0.7386	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7619	Phase 3
0.7374	Intermediate Similarity	NPD7618	Phase 3
0.7356	Intermediate Similarity	NPD2096	Phase 2
0.7356	Intermediate Similarity	NPD2091	Phase 2
0.7355	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6492	Phase 2
0.7333	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD4511	Phase 1
0.7318	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4547	Phase 3
0.7305	Intermediate Similarity	NPD2720	Phase 1
0.7305	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7948	Phase 1
0.7278	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2580	Discontinued
0.7235	Intermediate Similarity	NPD3610	Approved
0.7235	Intermediate Similarity	NPD3609	Approved
0.7216	Intermediate Similarity	NPD5075	Discontinued
0.7209	Intermediate Similarity	NPD5100	Phase 3
0.7204	Intermediate Similarity	NPD5901	Discontinued
0.72	Intermediate Similarity	NPD5105	Approved
0.72	Intermediate Similarity	NPD5106	Approved
0.7193	Intermediate Similarity	NPD750	Phase 2
0.7184	Intermediate Similarity	NPD5898	Approved
0.7184	Intermediate Similarity	NPD5897	Approved
0.7184	Intermediate Similarity	NPD5473	Discontinued
0.7184	Intermediate Similarity	NPD5899	Approved
0.7179	Intermediate Similarity	NPD6554	Approved
0.7179	Intermediate Similarity	NPD45	Approved
0.7175	Intermediate Similarity	NPD6217	Discontinued
0.7168	Intermediate Similarity	NPD6159	Phase 2
0.7152	Intermediate Similarity	NPD2150	Discontinued
0.7151	Intermediate Similarity	NPD2565	Phase 2
0.7151	Intermediate Similarity	NPD2564	Approved
0.7143	Intermediate Similarity	NPD7469	Discontinued
0.7143	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2383	Phase 1
0.7135	Intermediate Similarity	NPD4948	Discontinued
0.7124	Intermediate Similarity	NPD3476	Approved
0.7124	Intermediate Similarity	NPD3475	Approved
0.712	Intermediate Similarity	NPD6248	Phase 2
0.712	Intermediate Similarity	NPD6249	Phase 2
0.7118	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1661	Suspended
0.7095	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD680	Discontinued
0.7086	Intermediate Similarity	NPD6452	Discontinued
0.7083	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1251	Discontinued
0.7074	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3404	Approved
0.7066	Intermediate Similarity	NPD5255	Approved
0.7063	Intermediate Similarity	NPD2006	Phase 2
0.7059	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD947	Approved
0.7055	Intermediate Similarity	NPD2430	Phase 2
0.7045	Intermediate Similarity	NPD4399	Phase 2
0.7039	Intermediate Similarity	NPD2118	Approved
0.7039	Intermediate Similarity	NPD2119	Approved
0.7035	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6828	Phase 2
0.7035	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8093	Discontinued
0.703	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3814	Phase 1
0.7022	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6664	Approved
0.7006	Intermediate Similarity	NPD1253	Approved
0.7006	Intermediate Similarity	NPD3320	Approved
0.7006	Intermediate Similarity	NPD1254	Approved
0.7006	Intermediate Similarity	NPD3318	Approved
0.7006	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3319	Phase 1
0.7006	Intermediate Similarity	NPD1255	Approved
0.7006	Intermediate Similarity	NPD1256	Approved
0.7	Intermediate Similarity	NPD4334	Discontinued
0.6989	Remote Similarity	NPD4600	Approved
0.6989	Remote Similarity	NPD702	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4601	Approved
0.6988	Remote Similarity	NPD3405	Phase 3
0.6978	Remote Similarity	NPD4615	Phase 2
0.6975	Remote Similarity	NPD5995	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4957	Phase 2
0.6957	Remote Similarity	NPD3525	Discontinued
0.6957	Remote Similarity	NPD3717	Discontinued
0.6949	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1038	Approved
0.694	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3117	Approved
0.6936	Remote Similarity	NPD3116	Approved
0.6935	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD991	Phase 2
0.6928	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5913	Phase 3
0.6923	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5003	Discontinued
0.6915	Remote Similarity	NPD8073	Approved
0.6914	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3813	Approved
0.691	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD8094	Discontinued
0.6899	Remote Similarity	NPD3864	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