NPASS Compound

Structure

NPC201763 OpenBabel07101719152D 35 39 0 0 1 0 0 0 0 0999 V2000 4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8997 -5.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6428 -5.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8289 -5.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 -4.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5417 -4.0385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 7 8 1 0 0 0 0 7 12 2 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 25 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 29 1 0 0 0 0 18 1 1 6 0 0 0 18 19 1 0 0 0 0 19 26 1 6 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 28 1 6 0 0 0 21 30 1 0 0 0 0 22 28 1 6 0 0 0 22 31 1 0 0 0 0 23 30 1 1 0 0 0 23 32 1 0 0 0 0 24 28 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 27 1 6 0 0 0 27 5 1 1 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 17 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.35
Volume:	523.332
LogP:	2.894
LogD:	3.132
LogS:	-3.361
# Rotatable Bonds:	5
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	6.046
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.75
MDCK Permeability:	1.592884109413717e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.358
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.823
Plasma Protein Binding (PPB):	93.36511993408203%
Volume Distribution (VD):	0.571
Pgp-substrate:	4.999350547790527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.331
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.734
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.382
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.699
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	3.285
Half-life (T1/2):	0.726

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.625
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.294
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.861
Carcinogencity:	0.728
Eye Corrosion:	0.035
Eye Irritation:	0.023
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC201763

Natural Product ID:	NPC201763
*Common Name:**	Quadrangularic Acid K
IUPAC Name:	n.a.
Synonyms:	Quadrangularic Acid K
Standard InCHIKey:	FHXLGIIQMAKDCP-CHXITZBTSA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-18(8-7-12-25(2,3)35)19-11-13-27(5)20-9-10-21-28(6,24(33)34)22(31)16-23(32)30(21)17-29(20,30)15-14-26(19,27)4/h7,12,18-23,31-32,35H,8-11,13-17H2,1-6H3,(H,33,34)/b12-7-/t18-,19-,20+,21+,22+,23+,26-,27+,28+,29+,30-/m1/s1
SMILES:	C[C@H](C/C=CC(C)(C)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@@](C)([C@H](C[C@@H]([C@]54C[C@@]35CC[C@]12C)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL473038
PubChem CID:	10814872
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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
ED50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	82.6	ug ml-1	PMID[504451]

☑ 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 NPC201763 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	200
0.1-0.2	1343
0.2-0.3	4696
0.3-0.4	9928
0.4-0.5	11945
0.5-0.6	6335
0.6-0.7	5768
0.7-0.8	2350
0.8-0.85	104
0.85-0.9	15
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC257082
0.9596	High Similarity	NPC263729
0.95	High Similarity	NPC163216
0.9406	High Similarity	NPC285298
0.9192	High Similarity	NPC193934
0.9192	High Similarity	NPC271980
0.91	High Similarity	NPC312900
0.899	High Similarity	NPC37047
0.899	High Similarity	NPC41971
0.899	High Similarity	NPC180733
0.8969	High Similarity	NPC288906
0.8969	High Similarity	NPC263135
0.8725	High Similarity	NPC222153
0.8713	High Similarity	NPC75941
0.8687	High Similarity	NPC234564
0.8614	High Similarity	NPC94906
0.8586	High Similarity	NPC84383
0.8586	High Similarity	NPC266899
0.8571	High Similarity	NPC477855
0.8529	High Similarity	NPC477052
0.8529	High Similarity	NPC477051
0.8529	High Similarity	NPC477053
0.8529	High Similarity	NPC71706
0.8515	High Similarity	NPC119036
0.8515	High Similarity	NPC477854
0.8515	High Similarity	NPC472028
0.85	High Similarity	NPC477853
0.85	High Similarity	NPC195366
0.85	High Similarity	NPC114743
0.85	High Similarity	NPC160056
0.85	High Similarity	NPC327788
0.8447	Intermediate Similarity	NPC124544
0.8447	Intermediate Similarity	NPC477054
0.8431	Intermediate Similarity	NPC477521
0.8431	Intermediate Similarity	NPC470074
0.8416	Intermediate Similarity	NPC156546
0.84	Intermediate Similarity	NPC279974
0.84	Intermediate Similarity	NPC266431
0.8396	Intermediate Similarity	NPC472218
0.8396	Intermediate Similarity	NPC472217
0.8396	Intermediate Similarity	NPC472219
0.8364	Intermediate Similarity	NPC469794
0.8364	Intermediate Similarity	NPC72772
0.8351	Intermediate Similarity	NPC146937
0.835	Intermediate Similarity	NPC472924
0.835	Intermediate Similarity	NPC282524
0.8333	Intermediate Similarity	NPC302111
0.8317	Intermediate Similarity	NPC29152
0.8302	Intermediate Similarity	NPC472925
0.8286	Intermediate Similarity	NPC474281
0.8286	Intermediate Similarity	NPC72255
0.8283	Intermediate Similarity	NPC275671
0.8265	Intermediate Similarity	NPC128496
0.8265	Intermediate Similarity	NPC56962
0.8265	Intermediate Similarity	NPC474704
0.8265	Intermediate Similarity	NPC475921
0.8265	Intermediate Similarity	NPC24705
0.8235	Intermediate Similarity	NPC472851
0.823	Intermediate Similarity	NPC184555
0.8218	Intermediate Similarity	NPC476174
0.82	Intermediate Similarity	NPC477520
0.82	Intermediate Similarity	NPC476304
0.8198	Intermediate Similarity	NPC270929
0.819	Intermediate Similarity	NPC249187
0.819	Intermediate Similarity	NPC247957
0.819	Intermediate Similarity	NPC475050
0.8182	Intermediate Similarity	NPC469400
0.8163	Intermediate Similarity	NPC193360
0.8155	Intermediate Similarity	NPC191565
0.8155	Intermediate Similarity	NPC114274
0.8148	Intermediate Similarity	NPC173905
0.8148	Intermediate Similarity	NPC5475
0.8148	Intermediate Similarity	NPC284828
0.8148	Intermediate Similarity	NPC472216
0.8137	Intermediate Similarity	NPC173272
0.8137	Intermediate Similarity	NPC249954
0.8131	Intermediate Similarity	NPC64844
0.8131	Intermediate Similarity	NPC42847
0.8131	Intermediate Similarity	NPC477916
0.8119	Intermediate Similarity	NPC470958
0.8119	Intermediate Similarity	NPC469406
0.8119	Intermediate Similarity	NPC209662
0.8119	Intermediate Similarity	NPC470957
0.8119	Intermediate Similarity	NPC476186
0.8113	Intermediate Similarity	NPC471293
0.8113	Intermediate Similarity	NPC29705
0.8113	Intermediate Similarity	NPC160843
0.81	Intermediate Similarity	NPC198242
0.81	Intermediate Similarity	NPC110923
0.81	Intermediate Similarity	NPC211403
0.81	Intermediate Similarity	NPC74296
0.8091	Intermediate Similarity	NPC90952
0.8081	Intermediate Similarity	NPC57954
0.8081	Intermediate Similarity	NPC213832
0.8077	Intermediate Similarity	NPC471041
0.807	Intermediate Similarity	NPC476962
0.8061	Intermediate Similarity	NPC474684
0.8061	Intermediate Similarity	NPC142361
0.8058	Intermediate Similarity	NPC170978
0.8058	Intermediate Similarity	NPC320306
0.8058	Intermediate Similarity	NPC108078
0.8058	Intermediate Similarity	NPC469810
0.8058	Intermediate Similarity	NPC253586
0.8058	Intermediate Similarity	NPC189880
0.8053	Intermediate Similarity	NPC329736
0.8041	Intermediate Similarity	NPC470360
0.8039	Intermediate Similarity	NPC290481
0.8039	Intermediate Similarity	NPC272617
0.8039	Intermediate Similarity	NPC271195
0.8039	Intermediate Similarity	NPC48330
0.8039	Intermediate Similarity	NPC259286
0.8039	Intermediate Similarity	NPC88310
0.8039	Intermediate Similarity	NPC83693
0.8037	Intermediate Similarity	NPC37600
0.8037	Intermediate Similarity	NPC323834
0.8037	Intermediate Similarity	NPC257353
0.8037	Intermediate Similarity	NPC166607
0.8034	Intermediate Similarity	NPC293112
0.8021	Intermediate Similarity	NPC82623
0.802	Intermediate Similarity	NPC244356
0.802	Intermediate Similarity	NPC224060
0.8019	Intermediate Similarity	NPC72151
0.8019	Intermediate Similarity	NPC90177
0.8019	Intermediate Similarity	NPC112009
0.8018	Intermediate Similarity	NPC122056
0.8017	Intermediate Similarity	NPC55602
0.8017	Intermediate Similarity	NPC11895
0.8017	Intermediate Similarity	NPC469789
0.8	Intermediate Similarity	NPC270586
0.8	Intermediate Similarity	NPC46848
0.8	Intermediate Similarity	NPC472928
0.8	Intermediate Similarity	NPC289670
0.8	Intermediate Similarity	NPC121218
0.8	Intermediate Similarity	NPC253886
0.8	Intermediate Similarity	NPC476897
0.7982	Intermediate Similarity	NPC474901
0.7982	Intermediate Similarity	NPC475941
0.7982	Intermediate Similarity	NPC61520
0.7982	Intermediate Similarity	NPC476960
0.7981	Intermediate Similarity	NPC174663
0.798	Intermediate Similarity	NPC16377
0.798	Intermediate Similarity	NPC471900
0.7965	Intermediate Similarity	NPC55296
0.7965	Intermediate Similarity	NPC476959
0.7963	Intermediate Similarity	NPC83744
0.7963	Intermediate Similarity	NPC473284
0.7963	Intermediate Similarity	NPC59530
0.7961	Intermediate Similarity	NPC54248
0.7961	Intermediate Similarity	NPC471153
0.7961	Intermediate Similarity	NPC471903
0.7961	Intermediate Similarity	NPC276103
0.7961	Intermediate Similarity	NPC301534
0.7961	Intermediate Similarity	NPC250757
0.7961	Intermediate Similarity	NPC476327
0.7961	Intermediate Similarity	NPC476318
0.7961	Intermediate Similarity	NPC235053
0.7961	Intermediate Similarity	NPC329910
0.7959	Intermediate Similarity	NPC299068
0.7959	Intermediate Similarity	NPC70661
0.7949	Intermediate Similarity	NPC81736
0.7949	Intermediate Similarity	NPC172154
0.7949	Intermediate Similarity	NPC8369
0.7946	Intermediate Similarity	NPC470953
0.7944	Intermediate Similarity	NPC475036
0.7944	Intermediate Similarity	NPC209502
0.7944	Intermediate Similarity	NPC204833
0.7941	Intermediate Similarity	NPC279410
0.7941	Intermediate Similarity	NPC470385
0.7941	Intermediate Similarity	NPC292793
0.7941	Intermediate Similarity	NPC470386
0.7941	Intermediate Similarity	NPC469982
0.7941	Intermediate Similarity	NPC119562
0.7941	Intermediate Similarity	NPC60692
0.7941	Intermediate Similarity	NPC159365
0.7941	Intermediate Similarity	NPC8993
0.7941	Intermediate Similarity	NPC474529
0.7938	Intermediate Similarity	NPC476038
0.7938	Intermediate Similarity	NPC194937
0.7931	Intermediate Similarity	NPC170538
0.7928	Intermediate Similarity	NPC4573
0.7928	Intermediate Similarity	NPC475970
0.7928	Intermediate Similarity	NPC277769
0.7925	Intermediate Similarity	NPC475558
0.7925	Intermediate Similarity	NPC304832
0.7925	Intermediate Similarity	NPC473788
0.7925	Intermediate Similarity	NPC136289
0.7925	Intermediate Similarity	NPC88203
0.7925	Intermediate Similarity	NPC76866
0.7925	Intermediate Similarity	NPC148628
0.7925	Intermediate Similarity	NPC246736
0.7925	Intermediate Similarity	NPC275990
0.7925	Intermediate Similarity	NPC286519
0.7925	Intermediate Similarity	NPC214946
0.7925	Intermediate Similarity	NPC320447
0.7925	Intermediate Similarity	NPC293753
0.7925	Intermediate Similarity	NPC234892
0.7921	Intermediate Similarity	NPC288833
0.7921	Intermediate Similarity	NPC23217
0.7921	Intermediate Similarity	NPC189520
0.7921	Intermediate Similarity	NPC475708

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 NPC201763 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1625
0.2-0.3	3945
0.3-0.4	2234
0.4-0.5	678
0.5-0.6	197
0.6-0.7	212
0.7-0.8	89
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
0.7905	Intermediate Similarity	NPD7640	Approved
0.7905	Intermediate Similarity	NPD7639	Approved
0.781	Intermediate Similarity	NPD7638	Approved
0.7807	Intermediate Similarity	NPD7115	Discovery
0.7757	Intermediate Similarity	NPD5211	Phase 2
0.7745	Intermediate Similarity	NPD6079	Approved
0.7745	Intermediate Similarity	NPD7637	Suspended
0.7727	Intermediate Similarity	NPD6899	Approved
0.7727	Intermediate Similarity	NPD6881	Approved
0.7723	Intermediate Similarity	NPD5328	Approved
0.7706	Intermediate Similarity	NPD6402	Approved
0.7706	Intermediate Similarity	NPD5739	Approved
0.7706	Intermediate Similarity	NPD7128	Approved
0.7706	Intermediate Similarity	NPD6675	Approved
0.7677	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5697	Approved
0.7615	Intermediate Similarity	NPD5141	Approved
0.7589	Intermediate Similarity	NPD7290	Approved
0.7589	Intermediate Similarity	NPD4634	Approved
0.7589	Intermediate Similarity	NPD6883	Approved
0.7589	Intermediate Similarity	NPD7102	Approved
0.757	Intermediate Similarity	NPD5286	Approved
0.757	Intermediate Similarity	NPD4696	Approved
0.757	Intermediate Similarity	NPD5285	Approved
0.7568	Intermediate Similarity	NPD7320	Approved
0.7547	Intermediate Similarity	NPD4755	Approved
0.7541	Intermediate Similarity	NPD7319	Approved
0.7522	Intermediate Similarity	NPD8130	Phase 1
0.7522	Intermediate Similarity	NPD6617	Approved
0.7522	Intermediate Similarity	NPD6869	Approved
0.7522	Intermediate Similarity	NPD6650	Approved
0.7522	Intermediate Similarity	NPD6649	Approved
0.7522	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD5778	Approved
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.7477	Intermediate Similarity	NPD5701	Approved
0.7458	Intermediate Similarity	NPD6319	Approved
0.7456	Intermediate Similarity	NPD8297	Approved
0.7456	Intermediate Similarity	NPD6882	Approved
0.7453	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5222	Approved
0.7453	Intermediate Similarity	NPD5221	Approved
0.7431	Intermediate Similarity	NPD5224	Approved
0.7431	Intermediate Similarity	NPD5226	Approved
0.7431	Intermediate Similarity	NPD5225	Approved
0.7431	Intermediate Similarity	NPD4633	Approved
0.7411	Intermediate Similarity	NPD6011	Approved
0.7411	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4700	Approved
0.7404	Intermediate Similarity	NPD7515	Phase 2
0.74	Intermediate Similarity	NPD4786	Approved
0.7391	Intermediate Similarity	NPD4632	Approved
0.7383	Intermediate Similarity	NPD5173	Approved
0.7364	Intermediate Similarity	NPD5175	Approved
0.7364	Intermediate Similarity	NPD5174	Approved
0.7355	Intermediate Similarity	NPD7492	Approved
0.7347	Intermediate Similarity	NPD7525	Registered
0.7339	Intermediate Similarity	NPD5223	Approved
0.7333	Intermediate Similarity	NPD6399	Phase 3
0.732	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7736	Approved
0.7311	Intermediate Similarity	NPD6054	Approved
0.7295	Intermediate Similarity	NPD7507	Approved
0.7295	Intermediate Similarity	NPD6616	Approved
0.7292	Intermediate Similarity	NPD6117	Approved
0.729	Intermediate Similarity	NPD4697	Phase 3
0.7273	Intermediate Similarity	NPD7632	Discontinued
0.7273	Intermediate Similarity	NPD7604	Phase 2
0.7255	Intermediate Similarity	NPD3618	Phase 1
0.7238	Intermediate Similarity	NPD8035	Phase 2
0.7238	Intermediate Similarity	NPD6411	Approved
0.7238	Intermediate Similarity	NPD8034	Phase 2
0.7236	Intermediate Similarity	NPD7078	Approved
0.7232	Intermediate Similarity	NPD6008	Approved
0.7222	Intermediate Similarity	NPD6083	Phase 2
0.7222	Intermediate Similarity	NPD6084	Phase 2
0.7217	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6116	Phase 1
0.7203	Intermediate Similarity	NPD6009	Approved
0.72	Intermediate Similarity	NPD3667	Approved
0.719	Intermediate Similarity	NPD6370	Approved
0.717	Intermediate Similarity	NPD4202	Approved
0.7167	Intermediate Similarity	NPD6059	Approved
0.7107	Intermediate Similarity	NPD6015	Approved
0.7107	Intermediate Similarity	NPD6016	Approved
0.7105	Intermediate Similarity	NPD4730	Approved
0.7105	Intermediate Similarity	NPD4729	Approved
0.7103	Intermediate Similarity	NPD7748	Approved
0.71	Intermediate Similarity	NPD6902	Approved
0.7097	Intermediate Similarity	NPD8293	Discontinued
0.7087	Intermediate Similarity	NPD5786	Approved
0.7083	Intermediate Similarity	NPD7100	Approved
0.7083	Intermediate Similarity	NPD7101	Approved
0.7083	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4768	Approved
0.708	Intermediate Similarity	NPD4767	Approved
0.7054	Intermediate Similarity	NPD4754	Approved
0.7049	Intermediate Similarity	NPD5988	Approved
0.7048	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4753	Phase 2
0.7048	Intermediate Similarity	NPD6101	Approved
0.7043	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4269	Approved
0.703	Intermediate Similarity	NPD4270	Approved
0.701	Intermediate Similarity	NPD3703	Phase 2
0.7	Intermediate Similarity	NPD6931	Approved
0.7	Intermediate Similarity	NPD4225	Approved
0.7	Intermediate Similarity	NPD6335	Approved
0.7	Intermediate Similarity	NPD6930	Phase 2
0.7	Intermediate Similarity	NPD7514	Phase 3
0.6983	Remote Similarity	NPD5248	Approved
0.6983	Remote Similarity	NPD5250	Approved
0.6983	Remote Similarity	NPD5247	Approved
0.6983	Remote Similarity	NPD5251	Approved
0.6983	Remote Similarity	NPD5249	Phase 3
0.6975	Remote Similarity	NPD6274	Approved
0.6975	Remote Similarity	NPD6868	Approved
0.6967	Remote Similarity	NPD5983	Phase 2
0.6961	Remote Similarity	NPD6695	Phase 3
0.6957	Remote Similarity	NPD5128	Approved
0.6923	Remote Similarity	NPD5215	Approved
0.6923	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5217	Approved
0.6923	Remote Similarity	NPD5216	Approved
0.6917	Remote Similarity	NPD6317	Approved
0.6909	Remote Similarity	NPD7902	Approved
0.69	Remote Similarity	NPD6929	Approved
0.6893	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3665	Phase 1
0.6893	Remote Similarity	NPD3133	Approved
0.6893	Remote Similarity	NPD3666	Approved
0.6881	Remote Similarity	NPD5695	Phase 3
0.6881	Remote Similarity	NPD4629	Approved
0.6881	Remote Similarity	NPD5210	Approved
0.688	Remote Similarity	NPD6336	Discontinued
0.6864	Remote Similarity	NPD6053	Discontinued
0.686	Remote Similarity	NPD6313	Approved
0.686	Remote Similarity	NPD7328	Approved
0.686	Remote Similarity	NPD6314	Approved
0.686	Remote Similarity	NPD7327	Approved
0.6857	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5696	Approved
0.6838	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5169	Approved
0.6838	Remote Similarity	NPD5135	Approved
0.6832	Remote Similarity	NPD4252	Approved
0.6832	Remote Similarity	NPD7332	Phase 2
0.6832	Remote Similarity	NPD4819	Approved
0.6832	Remote Similarity	NPD5368	Approved
0.6832	Remote Similarity	NPD4821	Approved
0.6832	Remote Similarity	NPD4822	Approved
0.6832	Remote Similarity	NPD4820	Approved
0.6829	Remote Similarity	NPD6909	Approved
0.6829	Remote Similarity	NPD6908	Approved
0.6827	Remote Similarity	NPD5363	Approved
0.6822	Remote Similarity	NPD5785	Approved
0.681	Remote Similarity	NPD5168	Approved
0.6803	Remote Similarity	NPD7516	Approved
0.68	Remote Similarity	NPD7145	Approved
0.6796	Remote Similarity	NPD4788	Approved
0.6796	Remote Similarity	NPD5362	Discontinued
0.6792	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6672	Approved
0.6792	Remote Similarity	NPD5737	Approved
0.678	Remote Similarity	NPD5127	Approved
0.6765	Remote Similarity	NPD5369	Approved
0.6762	Remote Similarity	NPD6684	Approved
0.6762	Remote Similarity	NPD7334	Approved
0.6762	Remote Similarity	NPD7146	Approved
0.6762	Remote Similarity	NPD6409	Approved
0.6762	Remote Similarity	NPD5330	Approved
0.6762	Remote Similarity	NPD7521	Approved
0.6759	Remote Similarity	NPD5281	Approved
0.6759	Remote Similarity	NPD5284	Approved
0.6731	Remote Similarity	NPD3668	Phase 3
0.672	Remote Similarity	NPD8328	Phase 3
0.6701	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6925	Approved
0.67	Remote Similarity	NPD6932	Approved
0.67	Remote Similarity	NPD5776	Phase 2
0.6699	Remote Similarity	NPD4223	Phase 3
0.6699	Remote Similarity	NPD6435	Approved
0.6699	Remote Similarity	NPD4221	Approved
0.6698	Remote Similarity	NPD7524	Approved
0.6698	Remote Similarity	NPD7750	Discontinued
0.6698	Remote Similarity	NPD3573	Approved
0.6694	Remote Similarity	NPD8335	Approved
0.6694	Remote Similarity	NPD6291	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