NPASS Compound

Structure

NPC472491 OpenBabel07101719152D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.4238 -2.3837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7472 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1866 -1.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0672 -0.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2472 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8977 -1.5031 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6236 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1866 0.0889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6236 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4638 -0.6021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8886 -1.3689 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7472 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5201 -0.4236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7988 -1.7832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 20 1 0 0 0 0 11 18 1 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 1 0 0 0 13 16 2 0 0 0 0 14 10 1 1 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 17 22 2 0 0 0 0 18 2 1 1 0 0 0 19 3 1 1 0 0 0 20 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	341.348
LogP:	2.579
LogD:	1.884
LogS:	-4.36
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.78
Synthetic Accessibility Score:	5.571
Fsp3:	0.85
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:	-4.727
MDCK Permeability:	2.023611159529537e-05
Pgp-inhibitor:	0.907
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.509
Plasma Protein Binding (PPB):	94.36639404296875%
Volume Distribution (VD):	0.715
Pgp-substrate:	3.8322486877441406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.547
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.889
CYP3A4-substrate:	0.484

ADMET: Excretion

Clearance (CL):	7.189
Half-life (T1/2):	0.199

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.261
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.547
Skin Sensitization:	0.514
Carcinogencity:	0.456
Eye Corrosion:	0.004
Eye Irritation:	0.036
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC472491

Natural Product ID:	NPC472491
*Common Name:**	KPVLCOIEIVDRMQ-BLUZDYNSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KPVLCOIEIVDRMQ-BLUZDYNSSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-12-17(22)14-10-20(12,23)9-13-5-6-15-18(2,11-21)7-4-8-19(15,3)16(13)14/h12,14-15,21,23H,4-11H2,1-3H3/t12-,14+,15-,18-,19-,20-/m1/s1
SMILES:	OC[C@@]1(C)CCC[C@@]2([C@@H]1CCC1=C2[C@@H]2C[C@](C1)([C@@H](C2=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426499
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO32442	jungermannia fauriana	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]

☑ 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	14

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[515336]
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	>	50000.0	nM	PMID[515336]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	50000.0	nM	PMID[515336]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[515336]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[515336]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	50000.0	nM	PMID[515336]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[515336]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[515336]

☑ 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 NPC472491 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	166
0.1-0.2	1467
0.2-0.3	7225
0.3-0.4	15578
0.4-0.5	6686
0.5-0.6	6865
0.6-0.7	3728
0.7-0.8	868
0.8-0.85	94
0.85-0.9	12
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472494
0.9634	High Similarity	NPC472493
0.9625	High Similarity	NPC472492
0.9398	High Similarity	NPC472481
0.9398	High Similarity	NPC472484
0.9398	High Similarity	NPC472482
0.9176	High Similarity	NPC472489
0.9059	High Similarity	NPC472483
0.9036	High Similarity	NPC472480
0.8876	High Similarity	NPC472485
0.8837	High Similarity	NPC328313
0.8824	High Similarity	NPC472488
0.8736	High Similarity	NPC472475
0.8736	High Similarity	NPC472477
0.8621	High Similarity	NPC471724
0.8523	High Similarity	NPC76879
0.8506	High Similarity	NPC138756
0.8488	Intermediate Similarity	NPC474218
0.8452	Intermediate Similarity	NPC150506
0.8427	Intermediate Similarity	NPC472476
0.8409	Intermediate Similarity	NPC471722
0.8409	Intermediate Similarity	NPC53911
0.8391	Intermediate Similarity	NPC72133
0.8391	Intermediate Similarity	NPC472479
0.8372	Intermediate Similarity	NPC221758
0.8372	Intermediate Similarity	NPC59453
0.8372	Intermediate Similarity	NPC82902
0.837	Intermediate Similarity	NPC95565
0.8353	Intermediate Similarity	NPC151519
0.8333	Intermediate Similarity	NPC23434
0.8315	Intermediate Similarity	NPC54689
0.8315	Intermediate Similarity	NPC472971
0.8315	Intermediate Similarity	NPC472970
0.8261	Intermediate Similarity	NPC263347
0.8242	Intermediate Similarity	NPC25750
0.8242	Intermediate Similarity	NPC243866
0.8222	Intermediate Similarity	NPC69622
0.8222	Intermediate Similarity	NPC136801
0.8214	Intermediate Similarity	NPC472490
0.8202	Intermediate Similarity	NPC143767
0.8202	Intermediate Similarity	NPC242864
0.8202	Intermediate Similarity	NPC131470
0.8182	Intermediate Similarity	NPC475022
0.8182	Intermediate Similarity	NPC474732
0.8182	Intermediate Similarity	NPC94755
0.8182	Intermediate Similarity	NPC51014
0.8182	Intermediate Similarity	NPC31564
0.8182	Intermediate Similarity	NPC469994
0.8182	Intermediate Similarity	NPC474733
0.8182	Intermediate Similarity	NPC145879
0.8182	Intermediate Similarity	NPC89077
0.8182	Intermediate Similarity	NPC20688
0.8182	Intermediate Similarity	NPC28252
0.8182	Intermediate Similarity	NPC222613
0.8182	Intermediate Similarity	NPC474778
0.8182	Intermediate Similarity	NPC118648
0.8182	Intermediate Similarity	NPC55309
0.8161	Intermediate Similarity	NPC161423
0.8161	Intermediate Similarity	NPC227064
0.8161	Intermediate Similarity	NPC329043
0.8161	Intermediate Similarity	NPC321187
0.8161	Intermediate Similarity	NPC58841
0.8161	Intermediate Similarity	NPC473246
0.814	Intermediate Similarity	NPC110780
0.814	Intermediate Similarity	NPC193347
0.8132	Intermediate Similarity	NPC150383
0.8111	Intermediate Similarity	NPC326627
0.8111	Intermediate Similarity	NPC2983
0.8111	Intermediate Similarity	NPC310010
0.8111	Intermediate Similarity	NPC275740
0.8111	Intermediate Similarity	NPC32830
0.8111	Intermediate Similarity	NPC477943
0.8111	Intermediate Similarity	NPC474245
0.8111	Intermediate Similarity	NPC119416
0.8111	Intermediate Similarity	NPC86319
0.8105	Intermediate Similarity	NPC110149
0.809	Intermediate Similarity	NPC58063
0.809	Intermediate Similarity	NPC233836
0.809	Intermediate Similarity	NPC317590
0.809	Intermediate Similarity	NPC187376
0.809	Intermediate Similarity	NPC136548
0.809	Intermediate Similarity	NPC159046
0.809	Intermediate Similarity	NPC99909
0.809	Intermediate Similarity	NPC165895
0.809	Intermediate Similarity	NPC96496
0.809	Intermediate Similarity	NPC475740
0.8068	Intermediate Similarity	NPC102292
0.8068	Intermediate Similarity	NPC469948
0.8068	Intermediate Similarity	NPC474083
0.8068	Intermediate Similarity	NPC197823
0.8065	Intermediate Similarity	NPC162001
0.8065	Intermediate Similarity	NPC48330
0.8065	Intermediate Similarity	NPC473648
0.8065	Intermediate Similarity	NPC241156
0.8065	Intermediate Similarity	NPC222845
0.8065	Intermediate Similarity	NPC469599
0.8065	Intermediate Similarity	NPC200702
0.8065	Intermediate Similarity	NPC69548
0.8065	Intermediate Similarity	NPC184848
0.8065	Intermediate Similarity	NPC45324
0.8065	Intermediate Similarity	NPC127063
0.8046	Intermediate Similarity	NPC476082
0.8046	Intermediate Similarity	NPC278648
0.8043	Intermediate Similarity	NPC206810
0.8043	Intermediate Similarity	NPC152897
0.8043	Intermediate Similarity	NPC66429
0.8043	Intermediate Similarity	NPC470375
0.8043	Intermediate Similarity	NPC470376
0.8043	Intermediate Similarity	NPC134826
0.8043	Intermediate Similarity	NPC233118
0.8043	Intermediate Similarity	NPC250575
0.8043	Intermediate Similarity	NPC472942
0.8043	Intermediate Similarity	NPC474807
0.8023	Intermediate Similarity	NPC14151
0.8022	Intermediate Similarity	NPC469400
0.8022	Intermediate Similarity	NPC191684
0.8022	Intermediate Similarity	NPC183283
0.8022	Intermediate Similarity	NPC320026
0.8022	Intermediate Similarity	NPC171441
0.8	Intermediate Similarity	NPC474677
0.8	Intermediate Similarity	NPC44181
0.8	Intermediate Similarity	NPC328539
0.8	Intermediate Similarity	NPC186810
0.8	Intermediate Similarity	NPC193360
0.7979	Intermediate Similarity	NPC125622
0.7979	Intermediate Similarity	NPC173272
0.7979	Intermediate Similarity	NPC49371
0.7979	Intermediate Similarity	NPC155676
0.7979	Intermediate Similarity	NPC120708
0.7978	Intermediate Similarity	NPC155011
0.7978	Intermediate Similarity	NPC212843
0.7957	Intermediate Similarity	NPC111015
0.7957	Intermediate Similarity	NPC166906
0.7955	Intermediate Similarity	NPC85774
0.7955	Intermediate Similarity	NPC237712
0.7955	Intermediate Similarity	NPC214043
0.7955	Intermediate Similarity	NPC144258
0.7938	Intermediate Similarity	NPC473424
0.7935	Intermediate Similarity	NPC73457
0.7935	Intermediate Similarity	NPC475806
0.7935	Intermediate Similarity	NPC297265
0.7935	Intermediate Similarity	NPC154101
0.7935	Intermediate Similarity	NPC233116
0.7935	Intermediate Similarity	NPC63748
0.7931	Intermediate Similarity	NPC73882
0.7931	Intermediate Similarity	NPC260956
0.7931	Intermediate Similarity	NPC46881
0.7917	Intermediate Similarity	NPC316964
0.7917	Intermediate Similarity	NPC154072
0.7912	Intermediate Similarity	NPC186688
0.7912	Intermediate Similarity	NPC26959
0.7912	Intermediate Similarity	NPC268406
0.7912	Intermediate Similarity	NPC84271
0.7912	Intermediate Similarity	NPC473999
0.7912	Intermediate Similarity	NPC31985
0.7912	Intermediate Similarity	NPC476733
0.7912	Intermediate Similarity	NPC77168
0.7912	Intermediate Similarity	NPC1015
0.7912	Intermediate Similarity	NPC309603
0.7912	Intermediate Similarity	NPC102414
0.7912	Intermediate Similarity	NPC215029
0.7912	Intermediate Similarity	NPC122116
0.7912	Intermediate Similarity	NPC155479
0.7907	Intermediate Similarity	NPC472478
0.7895	Intermediate Similarity	NPC18509
0.7895	Intermediate Similarity	NPC190554
0.7889	Intermediate Similarity	NPC474684
0.7889	Intermediate Similarity	NPC90652
0.7889	Intermediate Similarity	NPC469317
0.7889	Intermediate Similarity	NPC312215
0.7889	Intermediate Similarity	NPC142361
0.7889	Intermediate Similarity	NPC241875
0.7889	Intermediate Similarity	NPC469314
0.7882	Intermediate Similarity	NPC178852
0.7872	Intermediate Similarity	NPC297199
0.7872	Intermediate Similarity	NPC472824
0.7872	Intermediate Similarity	NPC271195
0.7872	Intermediate Similarity	NPC259286
0.7872	Intermediate Similarity	NPC255809
0.7872	Intermediate Similarity	NPC470016
0.7872	Intermediate Similarity	NPC472932
0.7872	Intermediate Similarity	NPC317586
0.7865	Intermediate Similarity	NPC470574
0.7865	Intermediate Similarity	NPC202868
0.7865	Intermediate Similarity	NPC471224
0.7857	Intermediate Similarity	NPC117185
0.7857	Intermediate Similarity	NPC191892
0.7857	Intermediate Similarity	NPC55872
0.7857	Intermediate Similarity	NPC159442
0.7849	Intermediate Similarity	NPC69454
0.7841	Intermediate Similarity	NPC471036
0.7841	Intermediate Similarity	NPC291320
0.7841	Intermediate Similarity	NPC477852
0.7841	Intermediate Similarity	NPC474748
0.7841	Intermediate Similarity	NPC477373
0.7835	Intermediate Similarity	NPC473514
0.7826	Intermediate Similarity	NPC149761
0.7826	Intermediate Similarity	NPC20388
0.7826	Intermediate Similarity	NPC48010
0.7826	Intermediate Similarity	NPC261994

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 NPC472491 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1988
0.2-0.3	4380
0.3-0.4	1792
0.4-0.5	413
0.5-0.6	145
0.6-0.7	183
0.7-0.8	79
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8452	Intermediate Similarity	NPD4692	Approved
0.8452	Intermediate Similarity	NPD4139	Approved
0.8372	Intermediate Similarity	NPD4786	Approved
0.8353	Intermediate Similarity	NPD3667	Approved
0.8242	Intermediate Similarity	NPD4202	Approved
0.8182	Intermediate Similarity	NPD3618	Phase 1
0.8182	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD3133	Approved
0.8161	Intermediate Similarity	NPD3665	Phase 1
0.8161	Intermediate Similarity	NPD3666	Approved
0.814	Intermediate Similarity	NPD4221	Approved
0.814	Intermediate Similarity	NPD4223	Phase 3
0.8118	Intermediate Similarity	NPD4748	Discontinued
0.8111	Intermediate Similarity	NPD4753	Phase 2
0.7978	Intermediate Similarity	NPD5280	Approved
0.7978	Intermediate Similarity	NPD5690	Phase 2
0.7978	Intermediate Similarity	NPD4694	Approved
0.7955	Intermediate Similarity	NPD4197	Approved
0.7912	Intermediate Similarity	NPD5328	Approved
0.7895	Intermediate Similarity	NPD4755	Approved
0.7872	Intermediate Similarity	NPD5210	Approved
0.7872	Intermediate Similarity	NPD4629	Approved
0.7865	Intermediate Similarity	NPD5329	Approved
0.7841	Intermediate Similarity	NPD4788	Approved
0.7778	Intermediate Similarity	NPD4138	Approved
0.7778	Intermediate Similarity	NPD4688	Approved
0.7778	Intermediate Similarity	NPD5279	Phase 3
0.7778	Intermediate Similarity	NPD5205	Approved
0.7778	Intermediate Similarity	NPD4690	Approved
0.7778	Intermediate Similarity	NPD4693	Phase 3
0.7778	Intermediate Similarity	NPD4689	Approved
0.7742	Intermediate Similarity	NPD6079	Approved
0.7742	Intermediate Similarity	NPD5281	Approved
0.7742	Intermediate Similarity	NPD5284	Approved
0.7732	Intermediate Similarity	NPD4700	Approved
0.7732	Intermediate Similarity	NPD4696	Approved
0.7732	Intermediate Similarity	NPD5285	Approved
0.7732	Intermediate Similarity	NPD5286	Approved
0.7684	Intermediate Similarity	NPD5695	Phase 3
0.7674	Intermediate Similarity	NPD3617	Approved
0.766	Intermediate Similarity	NPD6399	Phase 3
0.7653	Intermediate Similarity	NPD5223	Approved
0.7647	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD4697	Phase 3
0.7576	Intermediate Similarity	NPD5225	Approved
0.7576	Intermediate Similarity	NPD5226	Approved
0.7576	Intermediate Similarity	NPD5224	Approved
0.7576	Intermediate Similarity	NPD4633	Approved
0.7576	Intermediate Similarity	NPD5211	Phase 2
0.7556	Intermediate Similarity	NPD3668	Phase 3
0.7526	Intermediate Similarity	NPD6084	Phase 2
0.7526	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD4754	Approved
0.7474	Intermediate Similarity	NPD5133	Approved
0.7449	Intermediate Similarity	NPD5696	Approved
0.7447	Intermediate Similarity	NPD4096	Approved
0.7426	Intermediate Similarity	NPD5141	Approved
0.7423	Intermediate Similarity	NPD5222	Approved
0.7423	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5221	Approved
0.7419	Intermediate Similarity	NPD4518	Approved
0.7404	Intermediate Similarity	NPD4634	Approved
0.7386	Intermediate Similarity	NPD4195	Approved
0.7381	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD6402	Approved
0.7353	Intermediate Similarity	NPD4768	Approved
0.7353	Intermediate Similarity	NPD7128	Approved
0.7353	Intermediate Similarity	NPD5739	Approved
0.7353	Intermediate Similarity	NPD4767	Approved
0.7349	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3698	Phase 2
0.7347	Intermediate Similarity	NPD5173	Approved
0.7326	Intermediate Similarity	NPD6942	Approved
0.7326	Intermediate Similarity	NPD7339	Approved
0.7308	Intermediate Similarity	NPD6373	Approved
0.7308	Intermediate Similarity	NPD6372	Approved
0.7284	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5697	Approved
0.7282	Intermediate Similarity	NPD5701	Approved
0.7263	Intermediate Similarity	NPD5207	Approved
0.7262	Intermediate Similarity	NPD4244	Approved
0.7262	Intermediate Similarity	NPD4245	Approved
0.7229	Intermediate Similarity	NPD5360	Phase 3
0.7229	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6011	Approved
0.7212	Intermediate Similarity	NPD5128	Approved
0.7212	Intermediate Similarity	NPD7320	Approved
0.7212	Intermediate Similarity	NPD4730	Approved
0.7212	Intermediate Similarity	NPD6899	Approved
0.7212	Intermediate Similarity	NPD6881	Approved
0.7212	Intermediate Similarity	NPD4729	Approved
0.7209	Intermediate Similarity	NPD4784	Approved
0.7209	Intermediate Similarity	NPD4785	Approved
0.7204	Intermediate Similarity	NPD7521	Approved
0.7204	Intermediate Similarity	NPD7334	Approved
0.7204	Intermediate Similarity	NPD6684	Approved
0.7204	Intermediate Similarity	NPD6098	Approved
0.7204	Intermediate Similarity	NPD7146	Approved
0.7204	Intermediate Similarity	NPD6409	Approved
0.7204	Intermediate Similarity	NPD5330	Approved
0.7176	Intermediate Similarity	NPD4243	Approved
0.717	Intermediate Similarity	NPD6649	Approved
0.717	Intermediate Similarity	NPD6650	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7525	Registered
0.7083	Intermediate Similarity	NPD5692	Phase 3
0.7075	Intermediate Similarity	NPD5251	Approved
0.7075	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5135	Approved
0.7075	Intermediate Similarity	NPD6883	Approved
0.7075	Intermediate Similarity	NPD5250	Approved
0.7075	Intermediate Similarity	NPD5248	Approved
0.7075	Intermediate Similarity	NPD5249	Phase 3
0.7075	Intermediate Similarity	NPD5169	Approved
0.7075	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD7290	Approved
0.7075	Intermediate Similarity	NPD5247	Approved
0.7059	Intermediate Similarity	NPD4789	Approved
0.7053	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5208	Approved
0.7053	Intermediate Similarity	NPD6903	Approved
0.7041	Intermediate Similarity	NPD6001	Approved
0.7033	Intermediate Similarity	NPD5369	Approved
0.7019	Intermediate Similarity	NPD6008	Approved
0.7011	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5694	Approved
0.701	Intermediate Similarity	NPD6050	Approved
0.701	Intermediate Similarity	NPD7515	Phase 2
0.7009	Intermediate Similarity	NPD5215	Approved
0.7009	Intermediate Similarity	NPD5127	Approved
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD5217	Approved
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6617	Approved
0.7009	Intermediate Similarity	NPD5216	Approved
0.7	Intermediate Similarity	NPD7115	Discovery
0.6979	Remote Similarity	NPD6904	Approved
0.6979	Remote Similarity	NPD6673	Approved
0.6979	Remote Similarity	NPD6080	Approved
0.6977	Remote Similarity	NPD4758	Discontinued
0.6944	Remote Similarity	NPD8297	Approved
0.6944	Remote Similarity	NPD6882	Approved
0.6932	Remote Similarity	NPD4190	Phase 3
0.6932	Remote Similarity	NPD3702	Approved
0.6932	Remote Similarity	NPD3703	Phase 2
0.6932	Remote Similarity	NPD5275	Approved
0.6923	Remote Similarity	NPD4695	Discontinued
0.6893	Remote Similarity	NPD5091	Approved
0.6881	Remote Similarity	NPD4632	Approved
0.6875	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.686	Remote Similarity	NPD4747	Approved
0.6854	Remote Similarity	NPD6117	Approved
0.6842	Remote Similarity	NPD4623	Approved
0.6842	Remote Similarity	NPD4519	Discontinued
0.6837	Remote Similarity	NPD5693	Phase 1
0.6837	Remote Similarity	NPD8035	Phase 2
0.6837	Remote Similarity	NPD8034	Phase 2
0.6837	Remote Similarity	NPD6411	Approved
0.6818	Remote Similarity	NPD5167	Approved
0.6818	Remote Similarity	NPD4687	Approved
0.6818	Remote Similarity	NPD6926	Approved
0.6818	Remote Similarity	NPD5733	Approved
0.6818	Remote Similarity	NPD6924	Approved
0.6814	Remote Similarity	NPD6054	Approved
0.6814	Remote Similarity	NPD6319	Approved
0.6814	Remote Similarity	NPD6059	Approved
0.68	Remote Similarity	NPD5654	Approved
0.6782	Remote Similarity	NPD5276	Approved
0.6778	Remote Similarity	NPD6116	Phase 1
0.6774	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD4269	Approved
0.6757	Remote Similarity	NPD6274	Approved
0.6754	Remote Similarity	NPD6015	Approved
0.6754	Remote Similarity	NPD6016	Approved
0.6744	Remote Similarity	NPD4137	Phase 3
0.6729	Remote Similarity	NPD5168	Approved
0.6703	Remote Similarity	NPD6118	Approved
0.6703	Remote Similarity	NPD3671	Phase 1
0.6703	Remote Similarity	NPD6114	Approved
0.6703	Remote Similarity	NPD6115	Approved
0.6703	Remote Similarity	NPD6697	Approved
0.67	Remote Similarity	NPD7748	Approved
0.6696	Remote Similarity	NPD6370	Approved
0.6696	Remote Similarity	NPD5988	Approved
0.6696	Remote Similarity	NPD6317	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5959	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