NPASS Compound

Structure

NPC32494 OpenBabel07101718312D 29 31 0 0 1 0 0 0 0 0999 V2000 -1.3803 2.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9727 4.3941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1428 2.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6820 2.8291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2539 -1.5576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2826 -0.6029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6040 0.2802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4507 1.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1463 3.4093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 1.7660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0566 1.9019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8350 0.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 1.4397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4936 -0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0860 3.0673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1107 -0.4962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -0.7660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0469 1.7628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8521 3.7101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0504 -0.8382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0406 1.9992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4410 1.1139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2597 2.0825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2816 -1.0554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 6 7 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 26 1 0 0 0 0 11 18 1 0 0 0 0 12 21 1 1 0 0 0 13 22 2 0 0 0 0 13 26 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 1 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 24 2 0 0 0 0 19 28 1 0 0 0 0 20 5 1 1 0 0 0 20 29 1 0 0 0 0 21 25 1 1 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.16
Volume:	400.606
LogP:	2.64
LogD:	2.034
LogS:	-3.25
# Rotatable Bonds:	6
TPSA:	115.43
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	6.029
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.888
MDCK Permeability:	2.1037365513620898e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.086
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.318
Plasma Protein Binding (PPB):	81.30901336669922%
Volume Distribution (VD):	1.066
Pgp-substrate:	18.62380599975586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.433
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.376
CYP2C9-inhibitor:	0.363
CYP2C9-substrate:	0.138
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.28
CYP3A4-substrate:	0.331

ADMET: Excretion

Clearance (CL):	11.149
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.406
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.852
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.836
Carcinogencity:	0.92
Eye Corrosion:	0.409
Eye Irritation:	0.159
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC32494

Natural Product ID:	NPC32494
*Common Name:**	YKIDGUZXBGGNBZ-GUNZAYKBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YKIDGUZXBGGNBZ-GUNZAYKBSA-N
Standard InCHI:	InChI=1S/C21H26O8/c1-11(2)18(23)27-15-8-12(3)21(25)7-6-20(5,29-21)9-16-17(15)14(19(24)28-16)10-26-13(4)22/h9,12,15,25H,1,6-8,10H2,2-5H3/b16-9+/t12-,15+,20-,21+/m1/s1
SMILES:	CC(=O)OCC1=C2[C@@H](OC(=O)C(=C)C)C[C@@H](C)[C@]3(O[C@](/C=C2/OC1=O)(C)CC3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2062866
PubChem CID:	70686496
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic 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
NPO33276	vernonia cinerea	Species	Asteraceae	Eukaryota	flower	n.a.	n.a.	PMID[22850207]

☑ 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	8
Others	4

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	99.2	%	PMID[501455]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	31.1	%	PMID[501455]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6600.0	nM	PMID[501455]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	95.1	%	PMID[501455]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	5200.0	nM	PMID[501456]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7700.0	nM	PMID[501456]
NPT2	Others	Unspecified		Inhibition	=	95.8	%	PMID[501455]
NPT2	Others	Unspecified		IC50	=	5200.0	nM	PMID[501455]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2600.0	nM	PMID[501456]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8300.0	nM	PMID[501456]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9100.0	nM	PMID[501456]
NPT27	Others	Unspecified		IC50	=	7100.0	nM	PMID[501456]

☑ 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 NPC32494 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	190
0.1-0.2	1169
0.2-0.3	4543
0.3-0.4	11407
0.4-0.5	15124
0.5-0.6	7021
0.6-0.7	2888
0.7-0.8	325
0.8-0.85	11
0.85-0.9	5
0.9-0.95	6
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC175842
0.9655	High Similarity	NPC59646
0.9545	High Similarity	NPC470521
0.9535	High Similarity	NPC242877
0.9535	High Similarity	NPC64913
0.9425	High Similarity	NPC3436
0.9318	High Similarity	NPC470520
0.931	High Similarity	NPC225283
0.9231	High Similarity	NPC471490
0.9011	High Similarity	NPC471492
0.8977	High Similarity	NPC260343
0.8817	High Similarity	NPC2666
0.871	High Similarity	NPC473333
0.8421	Intermediate Similarity	NPC471462
0.8222	Intermediate Similarity	NPC130030
0.8105	Intermediate Similarity	NPC474338
0.8081	Intermediate Similarity	NPC197835
0.8081	Intermediate Similarity	NPC189609
0.8081	Intermediate Similarity	NPC291500
0.8081	Intermediate Similarity	NPC303653
0.8081	Intermediate Similarity	NPC140591
0.7961	Intermediate Similarity	NPC38154
0.7938	Intermediate Similarity	NPC299396
0.7938	Intermediate Similarity	NPC301596
0.7778	Intermediate Similarity	NPC187268
0.7755	Intermediate Similarity	NPC172998
0.7742	Intermediate Similarity	NPC469483
0.7708	Intermediate Similarity	NPC158061
0.7653	Intermediate Similarity	NPC273197
0.7653	Intermediate Similarity	NPC234339
0.7634	Intermediate Similarity	NPC471185
0.7629	Intermediate Similarity	NPC189651
0.7629	Intermediate Similarity	NPC471483
0.7629	Intermediate Similarity	NPC475098
0.7579	Intermediate Similarity	NPC476805
0.7579	Intermediate Similarity	NPC475819
0.7576	Intermediate Similarity	NPC288350
0.7576	Intermediate Similarity	NPC173329
0.7576	Intermediate Similarity	NPC230800
0.7553	Intermediate Similarity	NPC204048
0.7553	Intermediate Similarity	NPC305475
0.7553	Intermediate Similarity	NPC475461
0.7553	Intermediate Similarity	NPC261721
0.7551	Intermediate Similarity	NPC469632
0.7529	Intermediate Similarity	NPC232812
0.7528	Intermediate Similarity	NPC315394
0.7526	Intermediate Similarity	NPC261607
0.7526	Intermediate Similarity	NPC111114
0.7526	Intermediate Similarity	NPC300312
0.7525	Intermediate Similarity	NPC469864
0.7525	Intermediate Similarity	NPC469872
0.75	Intermediate Similarity	NPC329852
0.7475	Intermediate Similarity	NPC471141
0.7474	Intermediate Similarity	NPC160138
0.7451	Intermediate Similarity	NPC469851
0.7449	Intermediate Similarity	NPC156553
0.7447	Intermediate Similarity	NPC470755
0.7447	Intermediate Similarity	NPC255307
0.7442	Intermediate Similarity	NPC37929
0.7442	Intermediate Similarity	NPC64234
0.7426	Intermediate Similarity	NPC203627
0.7419	Intermediate Similarity	NPC475947
0.74	Intermediate Similarity	NPC16967
0.7396	Intermediate Similarity	NPC469653
0.7396	Intermediate Similarity	NPC471047
0.7396	Intermediate Similarity	NPC469628
0.7396	Intermediate Similarity	NPC475906
0.7396	Intermediate Similarity	NPC471956
0.7396	Intermediate Similarity	NPC469631
0.7391	Intermediate Similarity	NPC325031
0.7391	Intermediate Similarity	NPC474894
0.7391	Intermediate Similarity	NPC78677
0.7391	Intermediate Similarity	NPC141810
0.7391	Intermediate Similarity	NPC8538
0.7391	Intermediate Similarity	NPC59994
0.7391	Intermediate Similarity	NPC315731
0.7391	Intermediate Similarity	NPC112868
0.7391	Intermediate Similarity	NPC184208
0.7386	Intermediate Similarity	NPC470686
0.7374	Intermediate Similarity	NPC256368
0.7374	Intermediate Similarity	NPC167219
0.7374	Intermediate Similarity	NPC191521
0.7374	Intermediate Similarity	NPC474247
0.7374	Intermediate Similarity	NPC477131
0.7374	Intermediate Similarity	NPC140543
0.7368	Intermediate Similarity	NPC162071
0.7368	Intermediate Similarity	NPC150755
0.7347	Intermediate Similarity	NPC2882
0.734	Intermediate Similarity	NPC475706
0.734	Intermediate Similarity	NPC158756
0.734	Intermediate Similarity	NPC114979
0.734	Intermediate Similarity	NPC191476
0.732	Intermediate Similarity	NPC295312
0.732	Intermediate Similarity	NPC212598
0.73	Intermediate Similarity	NPC304886
0.7292	Intermediate Similarity	NPC72513
0.7282	Intermediate Similarity	NPC219038
0.7282	Intermediate Similarity	NPC110443
0.7282	Intermediate Similarity	NPC128733
0.7282	Intermediate Similarity	NPC4637
0.7282	Intermediate Similarity	NPC185141
0.7282	Intermediate Similarity	NPC98859
0.7282	Intermediate Similarity	NPC133907
0.7282	Intermediate Similarity	NPC46998
0.7273	Intermediate Similarity	NPC475838
0.7273	Intermediate Similarity	NPC205034
0.7273	Intermediate Similarity	NPC228451
0.7273	Intermediate Similarity	NPC152778
0.7273	Intermediate Similarity	NPC469692
0.7273	Intermediate Similarity	NPC469645
0.7273	Intermediate Similarity	NPC475302
0.7273	Intermediate Similarity	NPC472954
0.7273	Intermediate Similarity	NPC476300
0.7273	Intermediate Similarity	NPC162615
0.7273	Intermediate Similarity	NPC125674
0.7264	Intermediate Similarity	NPC475074
0.7263	Intermediate Similarity	NPC261380
0.7263	Intermediate Similarity	NPC215364
0.7263	Intermediate Similarity	NPC11804
0.7263	Intermediate Similarity	NPC165162
0.7255	Intermediate Similarity	NPC141191
0.7255	Intermediate Similarity	NPC474440
0.7253	Intermediate Similarity	NPC93763
0.7253	Intermediate Similarity	NPC108816
0.7245	Intermediate Similarity	NPC475995
0.7245	Intermediate Similarity	NPC144133
0.7245	Intermediate Similarity	NPC177668
0.7245	Intermediate Similarity	NPC129419
0.7245	Intermediate Similarity	NPC475855
0.7245	Intermediate Similarity	NPC179394
0.7245	Intermediate Similarity	NPC474098
0.7245	Intermediate Similarity	NPC474232
0.7245	Intermediate Similarity	NPC80875
0.7245	Intermediate Similarity	NPC473448
0.7241	Intermediate Similarity	NPC315285
0.7234	Intermediate Similarity	NPC474809
0.7234	Intermediate Similarity	NPC131669
0.7234	Intermediate Similarity	NPC169575
0.7234	Intermediate Similarity	NPC16488
0.7234	Intermediate Similarity	NPC473390
0.7234	Intermediate Similarity	NPC475714
0.7234	Intermediate Similarity	NPC44261
0.7234	Intermediate Similarity	NPC40746
0.7234	Intermediate Similarity	NPC116543
0.7228	Intermediate Similarity	NPC279621
0.7222	Intermediate Similarity	NPC301525
0.7222	Intermediate Similarity	NPC469880
0.7222	Intermediate Similarity	NPC123360
0.7216	Intermediate Similarity	NPC472378
0.7216	Intermediate Similarity	NPC473658
0.7216	Intermediate Similarity	NPC475902
0.7216	Intermediate Similarity	NPC476803
0.7212	Intermediate Similarity	NPC149371
0.7212	Intermediate Similarity	NPC471599
0.7204	Intermediate Similarity	NPC281949
0.7204	Intermediate Similarity	NPC301477
0.7204	Intermediate Similarity	NPC25684
0.72	Intermediate Similarity	NPC477241
0.72	Intermediate Similarity	NPC476267
0.72	Intermediate Similarity	NPC121825
0.7191	Intermediate Similarity	NPC474758
0.7188	Intermediate Similarity	NPC469910
0.7188	Intermediate Similarity	NPC311163
0.7188	Intermediate Similarity	NPC284902
0.7188	Intermediate Similarity	NPC107787
0.7184	Intermediate Similarity	NPC288876
0.7174	Intermediate Similarity	NPC19841
0.7174	Intermediate Similarity	NPC471537
0.7174	Intermediate Similarity	NPC617
0.7172	Intermediate Similarity	NPC133698
0.717	Intermediate Similarity	NPC81630
0.717	Intermediate Similarity	NPC469852
0.7158	Intermediate Similarity	NPC141193
0.7158	Intermediate Similarity	NPC476804
0.7158	Intermediate Similarity	NPC96259
0.7158	Intermediate Similarity	NPC82297
0.7158	Intermediate Similarity	NPC115786
0.7157	Intermediate Similarity	NPC169205
0.7157	Intermediate Similarity	NPC475709
0.7143	Intermediate Similarity	NPC115179
0.7143	Intermediate Similarity	NPC472755
0.7143	Intermediate Similarity	NPC471225
0.7143	Intermediate Similarity	NPC68156
0.7143	Intermediate Similarity	NPC307092
0.7143	Intermediate Similarity	NPC268298
0.7143	Intermediate Similarity	NPC97516
0.7143	Intermediate Similarity	NPC106040
0.7143	Intermediate Similarity	NPC133450
0.7143	Intermediate Similarity	NPC471938
0.7129	Intermediate Similarity	NPC475659
0.7129	Intermediate Similarity	NPC209355
0.7129	Intermediate Similarity	NPC67584
0.7129	Intermediate Similarity	NPC193645
0.7129	Intermediate Similarity	NPC48803
0.7129	Intermediate Similarity	NPC275960
0.7129	Intermediate Similarity	NPC471142
0.7129	Intermediate Similarity	NPC90121
0.7129	Intermediate Similarity	NPC13924
0.7129	Intermediate Similarity	NPC36954
0.7128	Intermediate Similarity	NPC11383

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 NPC32494 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1552
0.2-0.3	3775
0.3-0.4	2609
0.4-0.5	744
0.5-0.6	261
0.6-0.7	46
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7423	Intermediate Similarity	NPD7838	Discovery
0.7129	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4225	Approved
0.6804	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5209	Approved
0.6733	Remote Similarity	NPD6698	Approved
0.6733	Remote Similarity	NPD46	Approved
0.6701	Remote Similarity	NPD7154	Phase 3
0.6699	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.66	Remote Similarity	NPD4251	Approved
0.66	Remote Similarity	NPD4250	Approved
0.6577	Remote Similarity	NPD6686	Approved
0.6571	Remote Similarity	NPD7839	Suspended
0.6569	Remote Similarity	NPD5785	Approved
0.6566	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6648	Approved
0.6471	Remote Similarity	NPD1695	Approved
0.646	Remote Similarity	NPD6371	Approved
0.6442	Remote Similarity	NPD5778	Approved
0.6442	Remote Similarity	NPD5779	Approved
0.6429	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5363	Approved
0.6392	Remote Similarity	NPD4820	Approved
0.6392	Remote Similarity	NPD4819	Approved
0.6392	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4822	Approved
0.6392	Remote Similarity	NPD4821	Approved
0.6348	Remote Similarity	NPD6053	Discontinued
0.6346	Remote Similarity	NPD7637	Suspended
0.6333	Remote Similarity	NPD7503	Approved
0.633	Remote Similarity	NPD5344	Discontinued
0.6311	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4756	Discovery
0.6238	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5362	Discontinued
0.6198	Remote Similarity	NPD8513	Phase 3
0.6198	Remote Similarity	NPD8515	Approved
0.6198	Remote Similarity	NPD8516	Approved
0.6198	Remote Similarity	NPD8517	Approved
0.619	Remote Similarity	NPD6411	Approved
0.6186	Remote Similarity	NPD4268	Approved
0.6186	Remote Similarity	NPD4271	Approved
0.6162	Remote Similarity	NPD5369	Approved
0.6134	Remote Similarity	NPD7505	Discontinued
0.61	Remote Similarity	NPD4269	Approved
0.61	Remote Similarity	NPD4270	Approved
0.6083	Remote Similarity	NPD7327	Approved
0.6083	Remote Similarity	NPD7328	Approved
0.6078	Remote Similarity	NPD1694	Approved
0.6066	Remote Similarity	NPD8033	Approved
0.604	Remote Similarity	NPD5332	Approved
0.604	Remote Similarity	NPD5331	Approved
0.6033	Remote Similarity	NPD7516	Approved
0.6019	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD7638	Approved
0.5984	Remote Similarity	NPD8377	Approved
0.5984	Remote Similarity	NPD7319	Approved
0.5984	Remote Similarity	NPD8294	Approved
0.598	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD7829	Approved
0.5968	Remote Similarity	NPD7830	Approved
0.5952	Remote Similarity	NPD8074	Phase 3
0.5946	Remote Similarity	NPD7639	Approved
0.5946	Remote Similarity	NPD7640	Approved
0.5941	Remote Similarity	NPD6435	Approved
0.5935	Remote Similarity	NPD8380	Approved
0.5935	Remote Similarity	NPD8379	Approved
0.5935	Remote Similarity	NPD8296	Approved
0.5935	Remote Similarity	NPD8335	Approved
0.5935	Remote Similarity	NPD8378	Approved
0.5909	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4252	Approved
0.5882	Remote Similarity	NPD6695	Phase 3
0.5876	Remote Similarity	NPD8039	Approved
0.5873	Remote Similarity	NPD7507	Approved
0.5868	Remote Similarity	NPD7500	Approved
0.5826	Remote Similarity	NPD4211	Phase 1
0.5798	Remote Similarity	NPD6882	Approved
0.5798	Remote Similarity	NPD969	Suspended
0.5763	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD2067	Discontinued
0.5748	Remote Similarity	NPD8451	Approved
0.5743	Remote Similarity	NPD5368	Approved
0.5727	Remote Similarity	NPD5695	Phase 3
0.5714	Remote Similarity	NPD2204	Approved
0.5714	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7642	Approved
0.5703	Remote Similarity	NPD8448	Approved
0.5701	Remote Similarity	NPD6051	Approved
0.5701	Remote Similarity	NPD5370	Suspended
0.57	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6399	Phase 3
0.568	Remote Similarity	NPD8444	Approved
0.5678	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD7492	Approved
0.566	Remote Similarity	NPD7524	Approved
0.566	Remote Similarity	NPD7750	Discontinued
0.5652	Remote Similarity	NPD6647	Phase 2
0.5652	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5697	Approved
0.5635	Remote Similarity	NPD8080	Discontinued
0.5625	Remote Similarity	NPD6083	Phase 2
0.5625	Remote Similarity	NPD6616	Approved
0.5625	Remote Similarity	NPD8273	Phase 1
0.5625	Remote Similarity	NPD6084	Phase 2
0.5612	Remote Similarity	NPD6924	Approved
0.5612	Remote Similarity	NPD6926	Approved
0.561	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6054	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