NPASS Compound

Structure

NPC469993 OpenBabel07101719512D 32 36 0 0 1 0 0 0 0 0999 V2000 7.1870 -1.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7216 -2.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 -1.0000 -0.0000 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 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 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 1 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 5.1962 -2.0000 0.0000 C 0 0 2 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 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 2 0 0 0 0 9 20 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 26 1 1 0 0 0 20 29 1 0 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 25 1 6 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 23 31 2 0 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 30 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	496.961
LogP:	6.051
LogD:	4.954
LogS:	-5.648
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	5.049
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.11
MDCK Permeability:	9.470527402299922e-06
Pgp-inhibitor:	0.138
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.616
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.878
Plasma Protein Binding (PPB):	96.31993865966797%
Volume Distribution (VD):	1.204
Pgp-substrate:	3.0140554904937744%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.824
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.179
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.106
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.928

ADMET: Excretion

Clearance (CL):	5.879
Half-life (T1/2):	0.257

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.515
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.527
Skin Sensitization:	0.528
Carcinogencity:	0.155
Eye Corrosion:	0.605
Eye Irritation:	0.444
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC469993

Natural Product ID:	NPC469993
*Common Name:**	4Alpha-Hydroxyfriedel-1-En-3-One
IUPAC Name:	(4S,4aS,6aS,6aS,6bR,8aR,12aR,14aR,14bS)-4-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-5,6,6a,7,8,9,10,12,12a,13,14,14b-dodecahydropicen-3-one
Synonyms:
Standard InCHIKey:	HVDFONKTLBTCGS-VAKVGTBTSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-24(2)13-14-25(3)15-17-27(5)21-11-12-29(7)20(9-10-23(31)30(29,8)32)26(21,4)16-18-28(27,6)22(25)19-24/h9-10,20-22,32H,11-19H2,1-8H3/t20-,21-,22+,25+,26-,27+,28-,29-,30+/m0/s1
SMILES:	CC1(CCC2(CCC3(C4CCC5(C(C4(CCC3(C2C1)C)C)C=CC(=O)C5(C)O)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641916
PubChem CID:	50900325
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO4744	Garcia parviflora	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20958014]
NPO4744	Garcia parviflora	Species	Euphorbiaceae	Eukaryota	n.a.	branch	n.a.	PMID[20958014]
NPO4744	Garcia parviflora	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20958014]
NPO4744	Garcia parviflora	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	41800.0	nM	PMID[513163]

☑ 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 NPC469993 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	203
0.1-0.2	1506
0.2-0.3	6595
0.3-0.4	15372
0.4-0.5	8563
0.5-0.6	6183
0.6-0.7	3400
0.7-0.8	786
0.8-0.85	70
0.85-0.9	17
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9024	High Similarity	NPC53733
0.8889	High Similarity	NPC18955
0.881	High Similarity	NPC474537
0.869	High Similarity	NPC96095
0.8675	High Similarity	NPC69101
0.8675	High Similarity	NPC251779
0.8675	High Similarity	NPC310989
0.8659	High Similarity	NPC476809
0.8659	High Similarity	NPC108955
0.8621	High Similarity	NPC68148
0.8621	High Similarity	NPC65615
0.8588	High Similarity	NPC33663
0.8556	High Similarity	NPC147232
0.8554	High Similarity	NPC162632
0.8554	High Similarity	NPC471898
0.8554	High Similarity	NPC263272
0.8554	High Similarity	NPC55869
0.8554	High Similarity	NPC473217
0.8554	High Similarity	NPC3915
0.8554	High Similarity	NPC267691
0.8554	High Similarity	NPC274050
0.8471	Intermediate Similarity	NPC180834
0.8444	Intermediate Similarity	NPC23170
0.8444	Intermediate Similarity	NPC160413
0.8434	Intermediate Similarity	NPC469637
0.8434	Intermediate Similarity	NPC2482
0.8415	Intermediate Similarity	NPC275494
0.8415	Intermediate Similarity	NPC471409
0.8409	Intermediate Similarity	NPC112454
0.8391	Intermediate Similarity	NPC93778
0.8372	Intermediate Similarity	NPC241512
0.8372	Intermediate Similarity	NPC6185
0.8354	Intermediate Similarity	NPC225467
0.8353	Intermediate Similarity	NPC70834
0.8353	Intermediate Similarity	NPC105803
0.8333	Intermediate Similarity	NPC263780
0.8333	Intermediate Similarity	NPC278459
0.8333	Intermediate Similarity	NPC225515
0.8313	Intermediate Similarity	NPC231431
0.8313	Intermediate Similarity	NPC16394
0.8295	Intermediate Similarity	NPC230387
0.8276	Intermediate Similarity	NPC94666
0.8256	Intermediate Similarity	NPC144258
0.8222	Intermediate Similarity	NPC174167
0.8222	Intermediate Similarity	NPC470036
0.8214	Intermediate Similarity	NPC287063
0.8214	Intermediate Similarity	NPC37038
0.8202	Intermediate Similarity	NPC477973
0.8193	Intermediate Similarity	NPC476808
0.8182	Intermediate Similarity	NPC73064
0.8171	Intermediate Similarity	NPC92080
0.8171	Intermediate Similarity	NPC1254
0.8161	Intermediate Similarity	NPC274724
0.8161	Intermediate Similarity	NPC132228
0.8161	Intermediate Similarity	NPC29447
0.8161	Intermediate Similarity	NPC133954
0.8161	Intermediate Similarity	NPC8518
0.8161	Intermediate Similarity	NPC263997
0.8161	Intermediate Similarity	NPC474680
0.814	Intermediate Similarity	NPC307258
0.8132	Intermediate Similarity	NPC211230
0.8125	Intermediate Similarity	NPC190035
0.8118	Intermediate Similarity	NPC142244
0.8118	Intermediate Similarity	NPC121984
0.8118	Intermediate Similarity	NPC475863
0.8111	Intermediate Similarity	NPC46441
0.8095	Intermediate Similarity	NPC215843
0.8095	Intermediate Similarity	NPC199595
0.8095	Intermediate Similarity	NPC27817
0.809	Intermediate Similarity	NPC206060
0.809	Intermediate Similarity	NPC1753
0.809	Intermediate Similarity	NPC474474
0.809	Intermediate Similarity	NPC474511
0.8072	Intermediate Similarity	NPC471899
0.8072	Intermediate Similarity	NPC165711
0.8072	Intermediate Similarity	NPC471897
0.8072	Intermediate Similarity	NPC107039
0.8068	Intermediate Similarity	NPC213412
0.8068	Intermediate Similarity	NPC74363
0.8068	Intermediate Similarity	NPC475862
0.8065	Intermediate Similarity	NPC157113
0.8065	Intermediate Similarity	NPC62516
0.8046	Intermediate Similarity	NPC237712
0.8046	Intermediate Similarity	NPC476412
0.8046	Intermediate Similarity	NPC53385
0.8043	Intermediate Similarity	NPC474882
0.8023	Intermediate Similarity	NPC193347
0.8023	Intermediate Similarity	NPC238991
0.8023	Intermediate Similarity	NPC302661
0.8023	Intermediate Similarity	NPC103486
0.8022	Intermediate Similarity	NPC65120
0.8022	Intermediate Similarity	NPC474525
0.8022	Intermediate Similarity	NPC272746
0.8022	Intermediate Similarity	NPC233455
0.8022	Intermediate Similarity	NPC145067
0.8022	Intermediate Similarity	NPC158030
0.8022	Intermediate Similarity	NPC4036
0.8022	Intermediate Similarity	NPC26865
0.8	Intermediate Similarity	NPC474700
0.8	Intermediate Similarity	NPC262043
0.8	Intermediate Similarity	NPC184663
0.8	Intermediate Similarity	NPC267517
0.7979	Intermediate Similarity	NPC473456
0.7978	Intermediate Similarity	NPC58063
0.7978	Intermediate Similarity	NPC470523
0.7978	Intermediate Similarity	NPC173089
0.7978	Intermediate Similarity	NPC158141
0.7976	Intermediate Similarity	NPC260385
0.7976	Intermediate Similarity	NPC280654
0.7976	Intermediate Similarity	NPC189485
0.7976	Intermediate Similarity	NPC30321
0.7976	Intermediate Similarity	NPC110094
0.7957	Intermediate Similarity	NPC777
0.7955	Intermediate Similarity	NPC133652
0.7955	Intermediate Similarity	NPC469948
0.7955	Intermediate Similarity	NPC33881
0.7952	Intermediate Similarity	NPC69143
0.7952	Intermediate Similarity	NPC89294
0.7938	Intermediate Similarity	NPC179208
0.7935	Intermediate Similarity	NPC295643
0.7935	Intermediate Similarity	NPC214756
0.7935	Intermediate Similarity	NPC272075
0.7931	Intermediate Similarity	NPC200752
0.7931	Intermediate Similarity	NPC291999
0.7931	Intermediate Similarity	NPC309309
0.7927	Intermediate Similarity	NPC22134
0.7927	Intermediate Similarity	NPC255168
0.7927	Intermediate Similarity	NPC162164
0.7912	Intermediate Similarity	NPC474209
0.7912	Intermediate Similarity	NPC475823
0.7912	Intermediate Similarity	NPC252737
0.7912	Intermediate Similarity	NPC85173
0.7907	Intermediate Similarity	NPC474085
0.7907	Intermediate Similarity	NPC470034
0.7889	Intermediate Similarity	NPC181225
0.7889	Intermediate Similarity	NPC473242
0.7889	Intermediate Similarity	NPC17733
0.7889	Intermediate Similarity	NPC472802
0.7889	Intermediate Similarity	NPC470524
0.7889	Intermediate Similarity	NPC290690
0.7889	Intermediate Similarity	NPC470629
0.7889	Intermediate Similarity	NPC474512
0.7882	Intermediate Similarity	NPC192329
0.7882	Intermediate Similarity	NPC170394
0.7875	Intermediate Similarity	NPC286814
0.7872	Intermediate Similarity	NPC473158
0.7865	Intermediate Similarity	NPC327115
0.7865	Intermediate Similarity	NPC145879
0.7865	Intermediate Similarity	NPC235341
0.7865	Intermediate Similarity	NPC95594
0.7865	Intermediate Similarity	NPC474732
0.7865	Intermediate Similarity	NPC474778
0.7865	Intermediate Similarity	NPC477579
0.7865	Intermediate Similarity	NPC158393
0.7865	Intermediate Similarity	NPC474733
0.7865	Intermediate Similarity	NPC51014
0.7865	Intermediate Similarity	NPC31564
0.7857	Intermediate Similarity	NPC257666
0.7857	Intermediate Similarity	NPC266193
0.7849	Intermediate Similarity	NPC148964
0.7849	Intermediate Similarity	NPC74751
0.7849	Intermediate Similarity	NPC474328
0.7849	Intermediate Similarity	NPC471207
0.7841	Intermediate Similarity	NPC156981
0.7841	Intermediate Similarity	NPC85774
0.7841	Intermediate Similarity	NPC312660
0.7841	Intermediate Similarity	NPC251170
0.7841	Intermediate Similarity	NPC214043
0.7831	Intermediate Similarity	NPC279666
0.7831	Intermediate Similarity	NPC192540
0.7826	Intermediate Similarity	NPC230064
0.7826	Intermediate Similarity	NPC38754
0.7816	Intermediate Similarity	NPC163236
0.7816	Intermediate Similarity	NPC48362
0.7816	Intermediate Similarity	NPC320514
0.7802	Intermediate Similarity	NPC69627
0.7802	Intermediate Similarity	NPC274330
0.7802	Intermediate Similarity	NPC143232
0.7802	Intermediate Similarity	NPC470588
0.7802	Intermediate Similarity	NPC198664
0.7802	Intermediate Similarity	NPC326627
0.7802	Intermediate Similarity	NPC474245
0.7802	Intermediate Similarity	NPC281524
0.7802	Intermediate Similarity	NPC310010
0.7802	Intermediate Similarity	NPC76879
0.7791	Intermediate Similarity	NPC104545
0.7791	Intermediate Similarity	NPC472478
0.7778	Intermediate Similarity	NPC102683
0.7778	Intermediate Similarity	NPC98442
0.7778	Intermediate Similarity	NPC171203
0.7778	Intermediate Similarity	NPC476409
0.7778	Intermediate Similarity	NPC307426
0.7778	Intermediate Similarity	NPC130577
0.7778	Intermediate Similarity	NPC88716
0.7778	Intermediate Similarity	NPC293564
0.7778	Intermediate Similarity	NPC142415
0.7778	Intermediate Similarity	NPC136948
0.7778	Intermediate Similarity	NPC71507
0.7778	Intermediate Similarity	NPC51700
0.7778	Intermediate Similarity	NPC68160

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 NPC469993 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1851
0.2-0.3	4063
0.3-0.4	2123
0.4-0.5	521
0.5-0.6	173
0.6-0.7	165
0.7-0.8	45
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8659	High Similarity	NPD4695	Discontinued
0.8409	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD5329	Approved
0.8276	Intermediate Similarity	NPD5690	Phase 2
0.8256	Intermediate Similarity	NPD4197	Approved
0.8023	Intermediate Similarity	NPD4221	Approved
0.8023	Intermediate Similarity	NPD4223	Phase 3
0.8022	Intermediate Similarity	NPD7515	Phase 2
0.7976	Intermediate Similarity	NPD3617	Approved
0.7865	Intermediate Similarity	NPD5280	Approved
0.7865	Intermediate Similarity	NPD4623	Approved
0.7865	Intermediate Similarity	NPD4519	Discontinued
0.7865	Intermediate Similarity	NPD4694	Approved
0.7849	Intermediate Similarity	NPD7748	Approved
0.7802	Intermediate Similarity	NPD4753	Phase 2
0.7766	Intermediate Similarity	NPD4629	Approved
0.7766	Intermediate Similarity	NPD5210	Approved
0.7674	Intermediate Similarity	NPD4195	Approved
0.7667	Intermediate Similarity	NPD5205	Approved
0.7667	Intermediate Similarity	NPD4689	Approved
0.7667	Intermediate Similarity	NPD4688	Approved
0.7667	Intermediate Similarity	NPD4693	Phase 3
0.7667	Intermediate Similarity	NPD4690	Approved
0.7667	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4138	Approved
0.764	Intermediate Similarity	NPD3133	Approved
0.764	Intermediate Similarity	NPD3665	Phase 1
0.764	Intermediate Similarity	NPD4786	Approved
0.764	Intermediate Similarity	NPD3666	Approved
0.7634	Intermediate Similarity	NPD6079	Approved
0.7614	Intermediate Similarity	NPD3667	Approved
0.7604	Intermediate Similarity	NPD7902	Approved
0.7582	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7614	Phase 1
0.75	Intermediate Similarity	NPD5221	Approved
0.7473	Intermediate Similarity	NPD3618	Phase 1
0.7473	Intermediate Similarity	NPD5279	Phase 3
0.7449	Intermediate Similarity	NPD4696	Approved
0.7449	Intermediate Similarity	NPD5286	Approved
0.7449	Intermediate Similarity	NPD5285	Approved
0.7423	Intermediate Similarity	NPD6083	Phase 2
0.7423	Intermediate Similarity	NPD5173	Approved
0.7423	Intermediate Similarity	NPD6084	Phase 2
0.7419	Intermediate Similarity	NPD5328	Approved
0.7419	Intermediate Similarity	NPD6904	Approved
0.7419	Intermediate Similarity	NPD6080	Approved
0.7419	Intermediate Similarity	NPD6673	Approved
0.7374	Intermediate Similarity	NPD5223	Approved
0.7349	Intermediate Similarity	NPD4691	Approved
0.7333	Intermediate Similarity	NPD4788	Approved
0.7312	Intermediate Similarity	NPD6672	Approved
0.7312	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5737	Approved
0.73	Intermediate Similarity	NPD5225	Approved
0.73	Intermediate Similarity	NPD5091	Approved
0.73	Intermediate Similarity	NPD5226	Approved
0.73	Intermediate Similarity	NPD4633	Approved
0.73	Intermediate Similarity	NPD5224	Approved
0.73	Intermediate Similarity	NPD5211	Phase 2
0.7294	Intermediate Similarity	NPD4058	Approved
0.7292	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7900	Approved
0.7283	Intermediate Similarity	NPD6098	Approved
0.7263	Intermediate Similarity	NPD5281	Approved
0.7263	Intermediate Similarity	NPD5284	Approved
0.7245	Intermediate Similarity	NPD4755	Approved
0.7229	Intermediate Similarity	NPD4137	Phase 3
0.7228	Intermediate Similarity	NPD5174	Approved
0.7228	Intermediate Similarity	NPD5175	Approved
0.7216	Intermediate Similarity	NPD5695	Phase 3
0.7188	Intermediate Similarity	NPD5133	Approved
0.7188	Intermediate Similarity	NPD4202	Approved
0.7172	Intermediate Similarity	NPD5696	Approved
0.7157	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7143	Intermediate Similarity	NPD4747	Approved
0.7128	Intermediate Similarity	NPD4518	Approved
0.7115	Intermediate Similarity	NPD6899	Approved
0.7115	Intermediate Similarity	NPD6881	Approved
0.7111	Intermediate Similarity	NPD8028	Phase 2
0.71	Intermediate Similarity	NPD4700	Approved
0.7097	Intermediate Similarity	NPD6684	Approved
0.7097	Intermediate Similarity	NPD7146	Approved
0.7097	Intermediate Similarity	NPD7334	Approved
0.7097	Intermediate Similarity	NPD7521	Approved
0.7097	Intermediate Similarity	NPD6409	Approved
0.7097	Intermediate Similarity	NPD5330	Approved
0.7093	Intermediate Similarity	NPD4784	Approved
0.7093	Intermediate Similarity	NPD4785	Approved
0.7083	Intermediate Similarity	NPD5694	Approved
0.7083	Intermediate Similarity	NPD6050	Approved
0.7083	Intermediate Similarity	NPD5693	Phase 1
0.7079	Intermediate Similarity	NPD7645	Phase 2
0.7073	Intermediate Similarity	NPD7331	Phase 2
0.7065	Intermediate Similarity	NPD3668	Phase 3
0.7019	Intermediate Similarity	NPD5697	Approved
0.701	Intermediate Similarity	NPD6399	Phase 3
0.6981	Remote Similarity	NPD7290	Approved
0.6981	Remote Similarity	NPD7102	Approved
0.6981	Remote Similarity	NPD6883	Approved
0.6979	Remote Similarity	NPD5692	Phase 3
0.6979	Remote Similarity	NPD4096	Approved
0.697	Remote Similarity	NPD7732	Phase 3
0.6952	Remote Similarity	NPD4729	Approved
0.6952	Remote Similarity	NPD4730	Approved
0.6952	Remote Similarity	NPD6011	Approved
0.6951	Remote Similarity	NPD7341	Phase 2
0.6947	Remote Similarity	NPD5208	Approved
0.6947	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD6675	Approved
0.6923	Remote Similarity	NPD4139	Approved
0.6923	Remote Similarity	NPD6402	Approved
0.6923	Remote Similarity	NPD4692	Approved
0.6923	Remote Similarity	NPD5739	Approved
0.6923	Remote Similarity	NPD7128	Approved
0.6916	Remote Similarity	NPD6649	Approved
0.6916	Remote Similarity	NPD6847	Approved
0.6916	Remote Similarity	NPD6869	Approved
0.6916	Remote Similarity	NPD6617	Approved
0.6916	Remote Similarity	NPD6650	Approved
0.6916	Remote Similarity	NPD8130	Phase 1
0.6897	Remote Similarity	NPD4687	Approved
0.6897	Remote Similarity	NPD5733	Approved
0.6893	Remote Similarity	NPD4754	Approved
0.6887	Remote Similarity	NPD6012	Approved
0.6887	Remote Similarity	NPD6013	Approved
0.6887	Remote Similarity	NPD6014	Approved
0.686	Remote Similarity	NPD4243	Approved
0.6852	Remote Similarity	NPD8297	Approved
0.6852	Remote Similarity	NPD6882	Approved
0.6822	Remote Similarity	NPD4634	Approved
0.6822	Remote Similarity	NPD5248	Approved
0.6822	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5247	Approved
0.6822	Remote Similarity	NPD5251	Approved
0.6822	Remote Similarity	NPD5169	Approved
0.6822	Remote Similarity	NPD5250	Approved
0.6822	Remote Similarity	NPD5135	Approved
0.6822	Remote Similarity	NPD5249	Phase 3
0.6813	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5207	Approved
0.6792	Remote Similarity	NPD7320	Approved
0.6792	Remote Similarity	NPD5168	Approved
0.6792	Remote Similarity	NPD5128	Approved
0.6762	Remote Similarity	NPD4768	Approved
0.6762	Remote Similarity	NPD4767	Approved
0.6759	Remote Similarity	NPD5216	Approved
0.6759	Remote Similarity	NPD5217	Approved
0.6759	Remote Similarity	NPD5215	Approved
0.6759	Remote Similarity	NPD5127	Approved
0.6744	Remote Similarity	NPD4789	Approved
0.6729	Remote Similarity	NPD6373	Approved
0.6729	Remote Similarity	NPD6372	Approved
0.6707	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5360	Phase 3
0.67	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6614	Approved
0.6698	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5276	Approved
0.6636	Remote Similarity	NPD4632	Approved
0.6632	Remote Similarity	NPD1696	Phase 3
0.6629	Remote Similarity	NPD6942	Approved
0.6629	Remote Similarity	NPD7339	Approved
0.6607	Remote Similarity	NPD7115	Discovery
0.6606	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6001	Approved
0.6577	Remote Similarity	NPD5167	Approved
0.6556	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6335	Approved
0.6542	Remote Similarity	NPD6412	Phase 2
0.6535	Remote Similarity	NPD5654	Approved
0.6518	Remote Similarity	NPD6868	Approved
0.6491	Remote Similarity	NPD7610	Discontinued
0.6491	Remote Similarity	NPD7101	Approved
0.6491	Remote Similarity	NPD7100	Approved
0.6489	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4224	Phase 2
0.646	Remote Similarity	NPD6317	Approved
0.646	Remote Similarity	NPD6009	Approved
0.6452	Remote Similarity	NPD7525	Registered
0.6444	Remote Similarity	NPD4190	Phase 3
0.6444	Remote Similarity	NPD5275	Approved
0.6442	Remote Similarity	NPD6404	Discontinued
0.6436	Remote Similarity	NPD5282	Discontinued
0.6435	Remote Similarity	NPD6054	Approved
0.6421	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8328	Phase 3
0.6408	Remote Similarity	NPD5959	Approved
0.6404	Remote Similarity	NPD6313	Approved
0.6404	Remote Similarity	NPD6314	Approved
0.64	Remote Similarity	NPD8034	Phase 2
0.64	Remote Similarity	NPD6411	Approved
0.64	Remote Similarity	NPD8035	Phase 2
0.6372	Remote Similarity	NPD6274	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