NPASS Compound

Structure

NPC470507 OpenBabel07101718302D 25 27 0 0 1 0 0 0 0 0999 V2000 2.0248 4.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3413 4.1817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3413 3.1817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0248 4.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2272 -0.2670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0932 0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3612 0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0932 1.2330 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 -1.5962 -2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3612 1.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2272 1.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0248 2.8157 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 0.5248 3.6817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0193 2.7111 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 -1.9563 -0.4158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 -2.8532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3164 1.2784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 11 2 0 0 0 0 8 13 2 0 0 0 0 9 12 1 0 0 0 0 9 14 2 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 16 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 10 1 6 0 0 0 15 18 1 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	339.16
Volume:	349.78
LogP:	2.142
LogD:	1.846
LogS:	-3.557
# Rotatable Bonds:	5
TPSA:	102.0
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	3.285
Fsp3:	0.263
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:	-5.143
MDCK Permeability:	1.1965777957811952e-05
Pgp-inhibitor:	0.29
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.796
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	97.16973114013672%
Volume Distribution (VD):	0.453
Pgp-substrate:	2.47337007522583%

ADMET: Metabolism

CYP1A2-inhibitor:	0.173
CYP1A2-substrate:	0.577
CYP2C19-inhibitor:	0.169
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.306
CYP2C9-substrate:	0.668
CYP2D6-inhibitor:	0.347
CYP2D6-substrate:	0.337
CYP3A4-inhibitor:	0.582
CYP3A4-substrate:	0.65

ADMET: Excretion

Clearance (CL):	3.197
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.356
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.712
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.127
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC470507

Natural Product ID:	NPC470507
*Common Name:**	Cristatumin A
IUPAC Name:	(3S,6Z)-3-(hydroxymethyl)-6-[[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]piperazine-2,5-dione
Synonyms:	Cristatumin A
Standard InCHIKey:	QIODLACTMHCZRD-MZLJFPOFSA-N
Standard InCHI:	InChI=1S/C19H21N3O3/c1-4-19(2,3)16-12(11-7-5-6-8-13(11)20-16)9-14-17(24)22-15(10-23)18(25)21-14/h4-9,15,20,23H,1,10H2,2-3H3,(H,21,25)(H,22,24)/b14-9-/t15-/m0/s1
SMILES:	CC(C)(C=C)C1=C(C2=CC=CC=C2N1)C=C3C(=O)NC(C(=O)N3)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048726
PubChem CID:	70682034
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
NPO32843	eurotium cristatum en-220	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22727636]

☑ 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
MIC	2
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	>	200000.0	nM	PMID[533209]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64.0	ug.mL-1	PMID[533208]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[533208]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	20.65	%	PMID[533209]

☑ 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 NPC470507 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	283
0.1-0.2	2931
0.2-0.3	15782
0.3-0.4	15982
0.4-0.5	3555
0.5-0.6	2329
0.6-0.7	1331
0.7-0.8	440
0.8-0.85	41
0.85-0.9	16
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC37548
0.9456	High Similarity	NPC38736
0.9448	High Similarity	NPC187951
0.9441	High Similarity	NPC242556
0.9195	High Similarity	NPC471458
0.9184	High Similarity	NPC124005
0.9103	High Similarity	NPC34508
0.9007	High Similarity	NPC285469
0.8954	High Similarity	NPC473320
0.8919	High Similarity	NPC129042
0.8882	High Similarity	NPC184476
0.8875	High Similarity	NPC270009
0.8839	High Similarity	NPC472587
0.8824	High Similarity	NPC299594
0.8797	High Similarity	NPC6982
0.8782	High Similarity	NPC470508
0.8774	High Similarity	NPC16667
0.8765	High Similarity	NPC192270
0.8696	High Similarity	NPC293472
0.8693	High Similarity	NPC207726
0.8679	High Similarity	NPC470498
0.8642	High Similarity	NPC472443
0.8634	High Similarity	NPC288785
0.8601	High Similarity	NPC22079
0.8599	High Similarity	NPC271734
0.8526	High Similarity	NPC67056
0.8516	High Similarity	NPC141353
0.85	High Similarity	NPC280548
0.8497	Intermediate Similarity	NPC105818
0.8497	Intermediate Similarity	NPC24678
0.8491	Intermediate Similarity	NPC54988
0.8485	Intermediate Similarity	NPC472444
0.8415	Intermediate Similarity	NPC215795
0.8415	Intermediate Similarity	NPC176199
0.8375	Intermediate Similarity	NPC49954
0.8375	Intermediate Similarity	NPC474561
0.8355	Intermediate Similarity	NPC159856
0.8355	Intermediate Similarity	NPC314372
0.8354	Intermediate Similarity	NPC68354
0.8344	Intermediate Similarity	NPC469762
0.8344	Intermediate Similarity	NPC472586
0.8343	Intermediate Similarity	NPC46413
0.8333	Intermediate Similarity	NPC2949
0.8302	Intermediate Similarity	NPC282231
0.828	Intermediate Similarity	NPC469785
0.8239	Intermediate Similarity	NPC279918
0.8232	Intermediate Similarity	NPC37423
0.8232	Intermediate Similarity	NPC275305
0.8224	Intermediate Similarity	NPC190296
0.821	Intermediate Similarity	NPC201700
0.821	Intermediate Similarity	NPC63751
0.8188	Intermediate Similarity	NPC325252
0.8176	Intermediate Similarity	NPC92796
0.8176	Intermediate Similarity	NPC135141
0.8163	Intermediate Similarity	NPC475450
0.8158	Intermediate Similarity	NPC63157
0.8158	Intermediate Similarity	NPC473868
0.8155	Intermediate Similarity	NPC163055
0.8153	Intermediate Similarity	NPC25008
0.8153	Intermediate Similarity	NPC469765
0.8153	Intermediate Similarity	NPC469763
0.8153	Intermediate Similarity	NPC469760
0.8153	Intermediate Similarity	NPC469786
0.8153	Intermediate Similarity	NPC259644
0.8153	Intermediate Similarity	NPC73952
0.8137	Intermediate Similarity	NPC311276
0.8137	Intermediate Similarity	NPC194640
0.8137	Intermediate Similarity	NPC40779
0.8121	Intermediate Similarity	NPC198988
0.8101	Intermediate Similarity	NPC75540
0.8101	Intermediate Similarity	NPC80597
0.8101	Intermediate Similarity	NPC70922
0.8101	Intermediate Similarity	NPC212376
0.8101	Intermediate Similarity	NPC211572
0.8098	Intermediate Similarity	NPC317430
0.8092	Intermediate Similarity	NPC59084
0.8069	Intermediate Similarity	NPC250361
0.8067	Intermediate Similarity	NPC218268
0.8061	Intermediate Similarity	NPC472123
0.8049	Intermediate Similarity	NPC194411
0.8042	Intermediate Similarity	NPC41174
0.8037	Intermediate Similarity	NPC160105
0.8036	Intermediate Similarity	NPC198339
0.8027	Intermediate Similarity	NPC473587
0.8026	Intermediate Similarity	NPC88097
0.8025	Intermediate Similarity	NPC102423
0.8025	Intermediate Similarity	NPC33421
0.8012	Intermediate Similarity	NPC189812
0.8012	Intermediate Similarity	NPC329688
0.8	Intermediate Similarity	NPC470440
0.7988	Intermediate Similarity	NPC154293
0.7974	Intermediate Similarity	NPC469768
0.7974	Intermediate Similarity	NPC469767
0.7974	Intermediate Similarity	NPC469784
0.7974	Intermediate Similarity	NPC469783
0.7974	Intermediate Similarity	NPC469761
0.7974	Intermediate Similarity	NPC469780
0.7974	Intermediate Similarity	NPC469779
0.7973	Intermediate Similarity	NPC475428
0.7959	Intermediate Similarity	NPC473762
0.7952	Intermediate Similarity	NPC313791
0.7941	Intermediate Similarity	NPC139291
0.7941	Intermediate Similarity	NPC19679
0.7941	Intermediate Similarity	NPC472108
0.7929	Intermediate Similarity	NPC91179
0.7927	Intermediate Similarity	NPC109447
0.7927	Intermediate Similarity	NPC470509
0.7922	Intermediate Similarity	NPC469766
0.7921	Intermediate Similarity	NPC32200
0.7919	Intermediate Similarity	NPC179365
0.7917	Intermediate Similarity	NPC151939
0.7917	Intermediate Similarity	NPC59269
0.7917	Intermediate Similarity	NPC248454
0.7908	Intermediate Similarity	NPC104483
0.7908	Intermediate Similarity	NPC73767
0.7901	Intermediate Similarity	NPC131718
0.7898	Intermediate Similarity	NPC21605
0.7898	Intermediate Similarity	NPC471957
0.7895	Intermediate Similarity	NPC125746
0.7895	Intermediate Similarity	NPC84911
0.7892	Intermediate Similarity	NPC158129
0.7882	Intermediate Similarity	NPC233936
0.787	Intermediate Similarity	NPC11126
0.7867	Intermediate Similarity	NPC473930
0.7861	Intermediate Similarity	NPC317030
0.7857	Intermediate Similarity	NPC115611
0.7848	Intermediate Similarity	NPC2272
0.7844	Intermediate Similarity	NPC314603
0.7844	Intermediate Similarity	NPC97525
0.784	Intermediate Similarity	NPC230869
0.7829	Intermediate Similarity	NPC261195
0.7829	Intermediate Similarity	NPC96102
0.7829	Intermediate Similarity	NPC29886
0.7824	Intermediate Similarity	NPC300688
0.7818	Intermediate Similarity	NPC49217
0.7805	Intermediate Similarity	NPC476118
0.7797	Intermediate Similarity	NPC133366
0.7792	Intermediate Similarity	NPC110126
0.7791	Intermediate Similarity	NPC228835
0.7785	Intermediate Similarity	NPC477134
0.7778	Intermediate Similarity	NPC302191
0.7778	Intermediate Similarity	NPC105127
0.7771	Intermediate Similarity	NPC204141
0.7765	Intermediate Similarity	NPC72980
0.7759	Intermediate Similarity	NPC204565
0.7756	Intermediate Similarity	NPC20144
0.774	Intermediate Similarity	NPC474177
0.7733	Intermediate Similarity	NPC48938
0.773	Intermediate Similarity	NPC475990
0.773	Intermediate Similarity	NPC41257
0.773	Intermediate Similarity	NPC318065
0.773	Intermediate Similarity	NPC206819
0.7722	Intermediate Similarity	NPC143872
0.7714	Intermediate Similarity	NPC65215
0.7714	Intermediate Similarity	NPC175474
0.7714	Intermediate Similarity	NPC173028
0.7709	Intermediate Similarity	NPC232130
0.7706	Intermediate Similarity	NPC326575
0.7697	Intermediate Similarity	NPC294693
0.7697	Intermediate Similarity	NPC271797
0.7697	Intermediate Similarity	NPC21174
0.7688	Intermediate Similarity	NPC53947
0.7688	Intermediate Similarity	NPC148592
0.7684	Intermediate Similarity	NPC304187
0.7684	Intermediate Similarity	NPC477166
0.7674	Intermediate Similarity	NPC314394
0.767	Intermediate Similarity	NPC206967
0.7669	Intermediate Similarity	NPC286427
0.7661	Intermediate Similarity	NPC213468
0.7654	Intermediate Similarity	NPC205403
0.7644	Intermediate Similarity	NPC280290
0.7644	Intermediate Similarity	NPC476319
0.764	Intermediate Similarity	NPC216713
0.7637	Intermediate Similarity	NPC300183
0.763	Intermediate Similarity	NPC472109
0.763	Intermediate Similarity	NPC472110
0.7628	Intermediate Similarity	NPC279081
0.7614	Intermediate Similarity	NPC34271
0.761	Intermediate Similarity	NPC288838
0.76	Intermediate Similarity	NPC474707
0.7593	Intermediate Similarity	NPC200214
0.759	Intermediate Similarity	NPC8104
0.7586	Intermediate Similarity	NPC472294
0.7571	Intermediate Similarity	NPC469470
0.7571	Intermediate Similarity	NPC469501
0.7569	Intermediate Similarity	NPC52557
0.7566	Intermediate Similarity	NPC82295
0.7564	Intermediate Similarity	NPC312092
0.7562	Intermediate Similarity	NPC201380
0.7562	Intermediate Similarity	NPC179787
0.7558	Intermediate Similarity	NPC219336
0.7558	Intermediate Similarity	NPC133261
0.7557	Intermediate Similarity	NPC17059
0.7557	Intermediate Similarity	NPC119700
0.7554	Intermediate Similarity	NPC98715
0.7544	Intermediate Similarity	NPC134586
0.7544	Intermediate Similarity	NPC267885
0.7543	Intermediate Similarity	NPC15102
0.7529	Intermediate Similarity	NPC64055
0.7529	Intermediate Similarity	NPC161861

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 NPC470507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	582
0.2-0.3	944
0.3-0.4	1499
0.4-0.5	2839
0.5-0.6	2320
0.6-0.7	677
0.7-0.8	113
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD4462	Approved
0.8742	High Similarity	NPD4463	Approved
0.8438	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD3505	Approved
0.8354	Intermediate Similarity	NPD3506	Approved
0.8303	Intermediate Similarity	NPD4079	Approved
0.8303	Intermediate Similarity	NPD4076	Approved
0.8199	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5021	Discontinued
0.8092	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD1326	Approved
0.8049	Intermediate Similarity	NPD1325	Approved
0.8039	Intermediate Similarity	NPD1592	Phase 3
0.8026	Intermediate Similarity	NPD786	Approved
0.7962	Intermediate Similarity	NPD3100	Discontinued
0.7939	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD5254	Discontinued
0.7929	Intermediate Similarity	NPD6595	Phase 3
0.7911	Intermediate Similarity	NPD3833	Phase 3
0.7911	Intermediate Similarity	NPD3835	Phase 3
0.7904	Intermediate Similarity	NPD5065	Approved
0.7879	Intermediate Similarity	NPD4638	Approved
0.7879	Intermediate Similarity	NPD4639	Approved
0.7879	Intermediate Similarity	NPD4640	Approved
0.7848	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD2144	Approved
0.7806	Intermediate Similarity	NPD1722	Approved
0.7805	Intermediate Similarity	NPD5138	Approved
0.7805	Intermediate Similarity	NPD5140	Approved
0.7799	Intermediate Similarity	NPD2172	Phase 1
0.7778	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD8386	Phase 2
0.7756	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5596	Phase 2
0.7719	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4128	Approved
0.7674	Intermediate Similarity	NPD3038	Discontinued
0.7667	Intermediate Similarity	NPD3654	Approved
0.7662	Intermediate Similarity	NPD1262	Discovery
0.7651	Intermediate Similarity	NPD2915	Discontinued
0.7647	Intermediate Similarity	NPD5104	Approved
0.7647	Intermediate Similarity	NPD2381	Approved
0.7647	Intermediate Similarity	NPD2380	Approved
0.7647	Intermediate Similarity	NPD2382	Approved
0.764	Intermediate Similarity	NPD6158	Phase 2
0.764	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3385	Approved
0.758	Intermediate Similarity	NPD5020	Approved
0.758	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3961	Discontinued
0.7557	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4075	Phase 2
0.7529	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5899	Approved
0.7514	Intermediate Similarity	NPD5898	Approved
0.7514	Intermediate Similarity	NPD5897	Approved
0.75	Intermediate Similarity	NPD1683	Approved
0.7485	Intermediate Similarity	NPD2837	Discontinued
0.7485	Intermediate Similarity	NPD482	Approved
0.7472	Intermediate Similarity	NPD4499	Approved
0.7458	Intermediate Similarity	NPD8431	Approved
0.7456	Intermediate Similarity	NPD2844	Phase 3
0.7455	Intermediate Similarity	NPD4326	Phase 2
0.7443	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2095	Phase 2
0.7429	Intermediate Similarity	NPD2094	Phase 2
0.7429	Intermediate Similarity	NPD2092	Phase 2
0.7425	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2882	Phase 1
0.7416	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7619	Phase 3
0.7403	Intermediate Similarity	NPD7618	Phase 3
0.7399	Intermediate Similarity	NPD4181	Approved
0.7386	Intermediate Similarity	NPD2096	Phase 2
0.7386	Intermediate Similarity	NPD2091	Phase 2
0.7381	Intermediate Similarity	NPD3323	Discontinued
0.7365	Intermediate Similarity	NPD1404	Approved
0.7365	Intermediate Similarity	NPD1403	Approved
0.736	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2383	Phase 1
0.7353	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2640	Approved
0.7353	Intermediate Similarity	NPD2641	Approved
0.7348	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4703	Approved
0.7346	Intermediate Similarity	NPD4702	Approved
0.7345	Intermediate Similarity	NPD5075	Discontinued
0.7337	Intermediate Similarity	NPD6249	Phase 2
0.7337	Intermediate Similarity	NPD6248	Phase 2
0.7333	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7948	Phase 1
0.7312	Intermediate Similarity	NPD4047	Discontinued
0.7297	Intermediate Similarity	NPD4601	Approved
0.7297	Intermediate Similarity	NPD4600	Approved
0.7294	Intermediate Similarity	NPD2642	Approved
0.7294	Intermediate Similarity	NPD2639	Approved
0.7283	Intermediate Similarity	NPD6492	Phase 2
0.7278	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3116	Approved
0.7267	Intermediate Similarity	NPD3117	Approved
0.7261	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5003	Discontinued
0.7225	Intermediate Similarity	NPD750	Phase 2
0.7222	Intermediate Similarity	NPD4334	Discontinued
0.7213	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6217	Discontinued
0.72	Intermediate Similarity	NPD6159	Phase 2
0.7197	Intermediate Similarity	NPD4880	Discontinued
0.7196	Intermediate Similarity	NPD3003	Approved
0.7186	Intermediate Similarity	NPD2150	Discontinued
0.7178	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3609	Approved
0.7168	Intermediate Similarity	NPD3610	Approved
0.7166	Intermediate Similarity	NPD4511	Phase 1
0.7143	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5913	Phase 3
0.7119	Intermediate Similarity	NPD5473	Discontinued
0.7118	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2480	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6554	Approved
0.7107	Intermediate Similarity	NPD45	Approved
0.7105	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3525	Discontinued
0.7097	Intermediate Similarity	NPD947	Approved
0.7095	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD8072	Approved
0.709	Intermediate Similarity	NPD5487	Phase 1
0.7088	Intermediate Similarity	NPD2565	Phase 2
0.7088	Intermediate Similarity	NPD2564	Approved
0.7083	Intermediate Similarity	NPD2580	Discontinued
0.7079	Intermediate Similarity	NPD4399	Phase 2
0.7073	Intermediate Similarity	NPD7469	Discontinued
0.7072	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6828	Phase 2
0.7068	Intermediate Similarity	NPD8322	Phase 2
0.7065	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1038	Approved
0.7059	Intermediate Similarity	NPD2175	Phase 3
0.7059	Intermediate Similarity	NPD1768	Approved
0.7059	Intermediate Similarity	NPD2177	Approved
0.7059	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3814	Phase 1
0.7059	Intermediate Similarity	NPD2176	Approved
0.7053	Intermediate Similarity	NPD5901	Discontinued
0.7053	Intermediate Similarity	NPD8272	Phase 2
0.7052	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3476	Approved
0.7051	Intermediate Similarity	NPD3475	Approved
0.7049	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5501	Discontinued
0.7044	Intermediate Similarity	NPD1255	Approved
0.7044	Intermediate Similarity	NPD1256	Approved
0.7044	Intermediate Similarity	NPD1253	Approved
0.7044	Intermediate Similarity	NPD1254	Approved
0.7039	Intermediate Similarity	NPD3318	Approved
0.7039	Intermediate Similarity	NPD3320	Approved
0.7039	Intermediate Similarity	NPD5106	Approved
0.7039	Intermediate Similarity	NPD3319	Phase 1
0.7039	Intermediate Similarity	NPD5105	Approved
0.7035	Intermediate Similarity	NPD2720	Phase 1
0.7035	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4547	Phase 3
0.703	Intermediate Similarity	NPD1661	Suspended
0.7029	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD43	Approved
0.7029	Intermediate Similarity	NPD6182	Approved
0.7022	Intermediate Similarity	NPD6452	Discontinued
0.7021	Intermediate Similarity	NPD4501	Approved
0.7021	Intermediate Similarity	NPD4500	Approved
0.7016	Intermediate Similarity	NPD7957	Phase 1
0.7016	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4615	Phase 2
0.7011	Intermediate Similarity	NPD4315	Phase 2
0.701	Intermediate Similarity	NPD7470	Discontinued
0.7006	Intermediate Similarity	NPD8123	Approved
0.7006	Intermediate Similarity	NPD8122	Approved
0.7	Intermediate Similarity	NPD5255	Approved
0.6994	Remote Similarity	NPD2006	Phase 2
0.6989	Remote Similarity	NPD2928	Phase 2
0.6988	Remote Similarity	NPD2430	Phase 2
0.6983	Remote Similarity	NPD4204	Approved
0.6983	Remote Similarity	NPD4203	Approved
0.6971	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2119	Approved
0.6968	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2118	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