NPASS Compound

Structure

NPC470509 OpenBabel07101718302D 26 27 0 0 0 0 0 0 0 0999 V2000 -1.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 5.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9855 3.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0074 3.8475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2946 2.6885 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 1.3383 3.1043 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6547 4.3827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6984 4.7985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 5.0064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 26 1 0 0 0 0 5 19 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 11 2 0 0 0 0 9 13 2 0 0 0 0 10 12 1 0 0 0 0 10 14 2 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 2 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 16 23 2 0 0 0 0 17 22 1 0 0 0 0 17 24 2 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.15
Volume:	364.49
LogP:	2.046
LogD:	2.209
LogS:	-3.526
# Rotatable Bonds:	8
TPSA:	114.61
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	3.283
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.881
MDCK Permeability:	2.237545959360432e-05
Pgp-inhibitor:	0.63
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.55
Plasma Protein Binding (PPB):	90.3279037475586%
Volume Distribution (VD):	0.41
Pgp-substrate:	4.489611625671387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.905
CYP1A2-substrate:	0.881
CYP2C19-inhibitor:	0.774
CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.439
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.218
CYP2D6-substrate:	0.744
CYP3A4-inhibitor:	0.798
CYP3A4-substrate:	0.464

ADMET: Excretion

Clearance (CL):	2.324
Half-life (T1/2):	0.525

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.164
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.282
Carcinogencity:	0.063
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC470509

Natural Product ID:	NPC470509
*Common Name:**	Cristatumin D
IUPAC Name:	methyl (Z)-3-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-2-(oxamoylamino)prop-2-enoate
Synonyms:	Cristatumin D
Standard InCHIKey:	WMAYXXXLOKRQKS-UVTDQMKNSA-N
Standard InCHI:	InChI=1S/C19H21N3O4/c1-5-19(2,3)15-12(11-8-6-7-9-13(11)21-15)10-14(18(25)26-4)22-17(24)16(20)23/h5-10,21H,1H2,2-4H3,(H2,20,23)(H,22,24)/b14-10-
SMILES:	COC(=O)/C(=C/c1c2ccccc2[nH]c1C(C=C)(C)C)/NC(=O)C(=O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048728
PubChem CID:	70684150
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:0000348] Peptides

*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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.0	mm	PMID[552747]

☑ 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 NPC470509 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	348
0.1-0.2	3203
0.2-0.3	13994
0.3-0.4	17727
0.4-0.5	3179
0.5-0.6	2540
0.6-0.7	1445
0.7-0.8	258
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8854	High Similarity	NPC299594
0.8634	High Similarity	NPC271734
0.8293	Intermediate Similarity	NPC8104
0.8217	Intermediate Similarity	NPC242556
0.805	Intermediate Similarity	NPC470440
0.8037	Intermediate Similarity	NPC471458
0.8012	Intermediate Similarity	NPC124005
0.8012	Intermediate Similarity	NPC37548
0.7927	Intermediate Similarity	NPC470507
0.7901	Intermediate Similarity	NPC79356
0.7901	Intermediate Similarity	NPC102592
0.7898	Intermediate Similarity	NPC280290
0.7874	Intermediate Similarity	NPC469896
0.7844	Intermediate Similarity	NPC473320
0.7818	Intermediate Similarity	NPC38736
0.7791	Intermediate Similarity	NPC187951
0.7778	Intermediate Similarity	NPC129042
0.7771	Intermediate Similarity	NPC184476
0.7714	Intermediate Similarity	NPC233050
0.7714	Intermediate Similarity	NPC276540
0.7688	Intermediate Similarity	NPC161861
0.7668	Intermediate Similarity	NPC477979
0.7667	Intermediate Similarity	NPC63199
0.7667	Intermediate Similarity	NPC111602
0.7667	Intermediate Similarity	NPC102338
0.7667	Intermediate Similarity	NPC196251
0.7657	Intermediate Similarity	NPC28848
0.7657	Intermediate Similarity	NPC14325
0.7628	Intermediate Similarity	NPC475450
0.7627	Intermediate Similarity	NPC275292
0.7627	Intermediate Similarity	NPC243381
0.7616	Intermediate Similarity	NPC41174
0.76	Intermediate Similarity	NPC151635
0.7598	Intermediate Similarity	NPC133003
0.7595	Intermediate Similarity	NPC198988
0.7578	Intermediate Similarity	NPC2949
0.7571	Intermediate Similarity	NPC91179
0.7571	Intermediate Similarity	NPC16659
0.7566	Intermediate Similarity	NPC132539
0.7564	Intermediate Similarity	NPC22079
0.7561	Intermediate Similarity	NPC478186
0.756	Intermediate Similarity	NPC285469
0.7554	Intermediate Similarity	NPC220151
0.7554	Intermediate Similarity	NPC19692
0.7547	Intermediate Similarity	NPC218268
0.7547	Intermediate Similarity	NPC325252
0.7545	Intermediate Similarity	NPC281094
0.7532	Intermediate Similarity	NPC250361
0.7531	Intermediate Similarity	NPC277157
0.753	Intermediate Similarity	NPC24678
0.753	Intermediate Similarity	NPC105818
0.7529	Intermediate Similarity	NPC6982
0.7514	Intermediate Similarity	NPC219336
0.7514	Intermediate Similarity	NPC11126
0.7514	Intermediate Similarity	NPC265710
0.75	Intermediate Similarity	NPC473587
0.7471	Intermediate Similarity	NPC471943
0.7469	Intermediate Similarity	NPC238499
0.7459	Intermediate Similarity	NPC94752
0.7459	Intermediate Similarity	NPC311858
0.7459	Intermediate Similarity	NPC160381
0.7458	Intermediate Similarity	NPC15573
0.7458	Intermediate Similarity	NPC217372
0.7458	Intermediate Similarity	NPC473380
0.7458	Intermediate Similarity	NPC145885
0.7458	Intermediate Similarity	NPC14113
0.7458	Intermediate Similarity	NPC84827
0.7458	Intermediate Similarity	NPC183662
0.7458	Intermediate Similarity	NPC240088
0.7452	Intermediate Similarity	NPC475428
0.7446	Intermediate Similarity	NPC55493
0.7444	Intermediate Similarity	NPC228835
0.7436	Intermediate Similarity	NPC473762
0.7435	Intermediate Similarity	NPC277350
0.7433	Intermediate Similarity	NPC470499
0.7432	Intermediate Similarity	NPC324091
0.7432	Intermediate Similarity	NPC206967
0.7411	Intermediate Similarity	NPC312645
0.7407	Intermediate Similarity	NPC88097
0.7405	Intermediate Similarity	NPC179365
0.7399	Intermediate Similarity	NPC115232
0.7394	Intermediate Similarity	NPC314372
0.7394	Intermediate Similarity	NPC159856
0.7391	Intermediate Similarity	NPC243716
0.7389	Intermediate Similarity	NPC470205
0.7386	Intermediate Similarity	NPC34508
0.7384	Intermediate Similarity	NPC214106
0.7384	Intermediate Similarity	NPC16667
0.738	Intermediate Similarity	NPC141454
0.7378	Intermediate Similarity	NPC190296
0.7377	Intermediate Similarity	NPC61435
0.7377	Intermediate Similarity	NPC213629
0.7374	Intermediate Similarity	NPC88110
0.7371	Intermediate Similarity	NPC65080
0.7362	Intermediate Similarity	NPC469780
0.7362	Intermediate Similarity	NPC469768
0.7362	Intermediate Similarity	NPC115611
0.7362	Intermediate Similarity	NPC469779
0.7362	Intermediate Similarity	NPC469761
0.7362	Intermediate Similarity	NPC469784
0.7362	Intermediate Similarity	NPC469783
0.7362	Intermediate Similarity	NPC469767
0.7362	Intermediate Similarity	NPC59084
0.7358	Intermediate Similarity	NPC266249
0.7358	Intermediate Similarity	NPC473930
0.7354	Intermediate Similarity	NPC214428
0.7348	Intermediate Similarity	NPC477003
0.7347	Intermediate Similarity	NPC89508
0.7341	Intermediate Similarity	NPC21174
0.7341	Intermediate Similarity	NPC271797
0.7341	Intermediate Similarity	NPC472587
0.7337	Intermediate Similarity	NPC200214
0.7326	Intermediate Similarity	NPC472293
0.7326	Intermediate Similarity	NPC245916
0.7318	Intermediate Similarity	NPC283219
0.7318	Intermediate Similarity	NPC248041
0.7318	Intermediate Similarity	NPC126709
0.7318	Intermediate Similarity	NPC270009
0.7317	Intermediate Similarity	NPC473868
0.7317	Intermediate Similarity	NPC469766
0.7317	Intermediate Similarity	NPC63157
0.7316	Intermediate Similarity	NPC471944
0.731	Intermediate Similarity	NPC76982
0.7305	Intermediate Similarity	NPC477134
0.7302	Intermediate Similarity	NPC192674
0.7302	Intermediate Similarity	NPC293917
0.7301	Intermediate Similarity	NPC73767
0.7301	Intermediate Similarity	NPC104483
0.7297	Intermediate Similarity	NPC129909
0.7297	Intermediate Similarity	NPC138370
0.7296	Intermediate Similarity	NPC118940
0.7294	Intermediate Similarity	NPC207726
0.7284	Intermediate Similarity	NPC84911
0.7283	Intermediate Similarity	NPC473666
0.7282	Intermediate Similarity	NPC123839
0.7268	Intermediate Similarity	NPC141612
0.7268	Intermediate Similarity	NPC135601
0.7268	Intermediate Similarity	NPC17273
0.7268	Intermediate Similarity	NPC235684
0.7263	Intermediate Similarity	NPC254240
0.7263	Intermediate Similarity	NPC128265
0.7263	Intermediate Similarity	NPC294909
0.7263	Intermediate Similarity	NPC312870
0.7263	Intermediate Similarity	NPC475151
0.7263	Intermediate Similarity	NPC199851
0.7262	Intermediate Similarity	NPC2272
0.7258	Intermediate Similarity	NPC472292
0.7253	Intermediate Similarity	NPC470003
0.7253	Intermediate Similarity	NPC284678
0.7251	Intermediate Similarity	NPC141353
0.7241	Intermediate Similarity	NPC478182
0.7241	Intermediate Similarity	NPC311276
0.724	Intermediate Similarity	NPC165599
0.7235	Intermediate Similarity	NPC259644
0.7235	Intermediate Similarity	NPC469763
0.7235	Intermediate Similarity	NPC469786
0.7235	Intermediate Similarity	NPC469765
0.7235	Intermediate Similarity	NPC25008
0.7235	Intermediate Similarity	NPC469760
0.7235	Intermediate Similarity	NPC73952
0.7232	Intermediate Similarity	NPC470498
0.7231	Intermediate Similarity	NPC477548
0.7231	Intermediate Similarity	NPC478158
0.7228	Intermediate Similarity	NPC17059
0.7222	Intermediate Similarity	NPC96102
0.7222	Intermediate Similarity	NPC6093
0.7222	Intermediate Similarity	NPC261195
0.7222	Intermediate Similarity	NPC12649
0.7222	Intermediate Similarity	NPC29886
0.7222	Intermediate Similarity	NPC213468
0.7219	Intermediate Similarity	NPC33421
0.7219	Intermediate Similarity	NPC472210
0.7219	Intermediate Similarity	NPC472295
0.7219	Intermediate Similarity	NPC247735
0.7219	Intermediate Similarity	NPC269886
0.7219	Intermediate Similarity	NPC81802
0.7211	Intermediate Similarity	NPC472297
0.7211	Intermediate Similarity	NPC472296
0.7209	Intermediate Similarity	NPC469762
0.7207	Intermediate Similarity	NPC288785
0.7207	Intermediate Similarity	NPC267885
0.7198	Intermediate Similarity	NPC143533
0.7195	Intermediate Similarity	NPC110126
0.7193	Intermediate Similarity	NPC211572
0.7193	Intermediate Similarity	NPC80597
0.7193	Intermediate Similarity	NPC75540
0.7193	Intermediate Similarity	NPC70922
0.7193	Intermediate Similarity	NPC212376
0.7191	Intermediate Similarity	NPC252572
0.7189	Intermediate Similarity	NPC46413
0.7189	Intermediate Similarity	NPC175474
0.7186	Intermediate Similarity	NPC36405
0.7186	Intermediate Similarity	NPC204141
0.7184	Intermediate Similarity	NPC194881
0.7181	Intermediate Similarity	NPC294693
0.7178	Intermediate Similarity	NPC105127
0.7175	Intermediate Similarity	NPC280548
0.7168	Intermediate Similarity	NPC135141
0.7168	Intermediate Similarity	NPC67056
0.7168	Intermediate Similarity	NPC92796

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 NPC470509 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	651
0.2-0.3	905
0.3-0.4	1749
0.4-0.5	2622
0.5-0.6	2426
0.6-0.7	551
0.7-0.8	52
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8466	Intermediate Similarity	NPD2915	Discontinued
0.8333	Intermediate Similarity	NPD5104	Approved
0.8103	Intermediate Similarity	NPD5075	Discontinued
0.7963	Intermediate Similarity	NPD3835	Phase 3
0.7963	Intermediate Similarity	NPD3833	Phase 3
0.775	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4462	Approved
0.7636	Intermediate Similarity	NPD4463	Approved
0.7513	Intermediate Similarity	NPD6176	Phase 1
0.7487	Intermediate Similarity	NPD6249	Phase 2
0.7487	Intermediate Similarity	NPD6248	Phase 2
0.7459	Intermediate Similarity	NPD5444	Phase 1
0.7423	Intermediate Similarity	NPD5020	Approved
0.7418	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4326	Phase 2
0.7377	Intermediate Similarity	NPD4334	Discontinued
0.7362	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5487	Phase 1
0.733	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD3961	Discontinued
0.7316	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD786	Approved
0.7299	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5003	Discontinued
0.7263	Intermediate Similarity	NPD4501	Approved
0.7263	Intermediate Similarity	NPD4500	Approved
0.7229	Intermediate Similarity	NPD5254	Discontinued
0.7222	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2172	Phase 1
0.7216	Intermediate Similarity	NPD2844	Phase 3
0.7212	Intermediate Similarity	NPD1592	Phase 3
0.7208	Intermediate Similarity	NPD7573	Discontinued
0.7207	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD2092	Phase 2
0.7198	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3320	Approved
0.7198	Intermediate Similarity	NPD2095	Phase 2
0.7198	Intermediate Similarity	NPD2094	Phase 2
0.7198	Intermediate Similarity	NPD3319	Phase 1
0.7198	Intermediate Similarity	NPD3318	Approved
0.7196	Intermediate Similarity	NPD6206	Phase 1
0.7181	Intermediate Similarity	NPD7619	Phase 3
0.7181	Intermediate Similarity	NPD7618	Phase 3
0.7178	Intermediate Similarity	NPD1262	Discovery
0.7169	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD2144	Approved
0.7166	Intermediate Similarity	NPD4315	Phase 2
0.7158	Intermediate Similarity	NPD2096	Phase 2
0.7158	Intermediate Similarity	NPD6261	Phase 3
0.7158	Intermediate Similarity	NPD2091	Phase 2
0.7157	Intermediate Similarity	NPD7470	Discontinued
0.7151	Intermediate Similarity	NPD2565	Phase 2
0.7151	Intermediate Similarity	NPD2564	Approved
0.7151	Intermediate Similarity	NPD482	Approved
0.7151	Intermediate Similarity	NPD4499	Approved
0.7111	Intermediate Similarity	NPD4075	Phase 2
0.7108	Intermediate Similarity	NPD1722	Approved
0.7092	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5809	Phase 3
0.7079	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3654	Approved
0.7059	Intermediate Similarity	NPD3100	Discontinued
0.7053	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3038	Discontinued
0.7045	Intermediate Similarity	NPD5140	Approved
0.7045	Intermediate Similarity	NPD5138	Approved
0.7033	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5913	Phase 3
0.702	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2510	Approved
0.7005	Intermediate Similarity	NPD2509	Approved
0.7	Intermediate Similarity	NPD4602	Approved
0.7	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5427	Suspended
0.6959	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1683	Approved
0.6939	Remote Similarity	NPD8282	Approved
0.6939	Remote Similarity	NPD8283	Approved
0.6939	Remote Similarity	NPD8272	Phase 2
0.6939	Remote Similarity	NPD56	Approved
0.6935	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5021	Discontinued
0.6919	Remote Similarity	NPD5596	Phase 2
0.6906	Remote Similarity	NPD750	Phase 2
0.6902	Remote Similarity	NPD5473	Discontinued
0.6902	Remote Similarity	NPD6452	Discontinued
0.6893	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3385	Approved
0.6889	Remote Similarity	NPD1325	Approved
0.6889	Remote Similarity	NPD1326	Approved
0.6885	Remote Similarity	NPD3505	Approved
0.6885	Remote Similarity	NPD3506	Approved
0.6884	Remote Similarity	NPD4506	Discontinued
0.6882	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7727	Phase 2
0.6872	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD8322	Phase 2
0.6862	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4079	Approved
0.6848	Remote Similarity	NPD4076	Approved
0.6847	Remote Similarity	NPD3394	Approved
0.6847	Remote Similarity	NPD3393	Approved
0.6847	Remote Similarity	NPD3389	Approved
0.6839	Remote Similarity	NPD2837	Discontinued
0.6836	Remote Similarity	NPD1404	Approved
0.6836	Remote Similarity	NPD1403	Approved
0.6834	Remote Similarity	NPD8423	Phase 2
0.6834	Remote Similarity	NPD8399	Phase 1
0.6821	Remote Similarity	NPD4600	Approved
0.6821	Remote Similarity	NPD4601	Approved
0.6818	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6595	Phase 3
0.6809	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6217	Discontinued
0.6804	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3777	Phase 3
0.6802	Remote Similarity	NPD2920	Discontinued
0.68	Remote Similarity	NPD5834	Phase 3
0.68	Remote Similarity	NPD5835	Phase 3
0.6798	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5632	Approved
0.6778	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2639	Approved
0.6778	Remote Similarity	NPD2642	Approved
0.6776	Remote Similarity	NPD4128	Approved
0.6776	Remote Similarity	NPD5065	Approved
0.6774	Remote Similarity	NPD3178	Discontinued
0.6768	Remote Similarity	NPD3947	Discontinued
0.6768	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6448	Phase 1
0.6757	Remote Similarity	NPD8386	Phase 2
0.6748	Remote Similarity	NPD6770	Approved
0.6747	Remote Similarity	NPD4880	Discontinued
0.6744	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2640	Approved
0.674	Remote Similarity	NPD2641	Approved
0.674	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7957	Phase 1
0.6734	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5475	Discontinued
0.672	Remote Similarity	NPD5899	Approved
0.672	Remote Similarity	NPD5898	Approved
0.672	Remote Similarity	NPD5897	Approved
0.6717	Remote Similarity	NPD8072	Approved
0.6716	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7970	Approved
0.6704	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4181	Approved
0.6703	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD1096	Discontinued
0.6701	Remote Similarity	NPD7817	Phase 1
0.67	Remote Similarity	NPD7454	Approved
0.67	Remote Similarity	NPD7455	Approved
0.6685	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD1038	Approved
0.6684	Remote Similarity	NPD4399	Phase 2
0.6683	Remote Similarity	NPD8114	Approved
0.6683	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8115	Approved
0.6683	Remote Similarity	NPD5901	Discontinued
0.6667	Remote Similarity	NPD2580	Discontinued
0.6667	Remote Similarity	NPD8073	Approved
0.6667	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3583	Phase 2
0.6667	Remote Similarity	NPD3323	Discontinued
0.6667	Remote Similarity	NPD7688	Phase 1
0.6667	Remote Similarity	NPD2880	Discontinued
0.665	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6044	Discontinued
0.6649	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5501	Discontinued
0.6646	Remote Similarity	NPD947	Approved
0.6634	Remote Similarity	NPD4897	Phase 2
0.6632	Remote Similarity	NPD7026	Phase 2
0.6632	Remote Similarity	NPD4922	Phase 2
0.6628	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7824	Approved
0.6619	Remote Similarity	NPD7716	Approved
0.6619	Remote Similarity	NPD7717	Approved
0.6618	Remote Similarity	NPD8405	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