NPASS Compound

Structure

NPC470965 OpenBabel07101718182D 37 36 0 0 1 0 0 0 0 0999 V2000 17.3205 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.4545 15.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 11.0000 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 12.1244 13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 10.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 14.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 15.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 8.0000 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 16.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 4.0000 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 14.7224 15.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 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 15.5885 16.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 5.5000 0.0000 C 0 0 3 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 15.5885 17.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 5.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 3 0 0 0 0 2 31 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 23 27 2 0 0 0 0 24 28 2 0 0 0 0 25 29 1 0 0 0 0 26 30 3 0 0 0 0 27 31 1 0 0 0 0 28 32 1 0 0 0 0 29 32 1 0 0 0 0 30 33 1 0 0 0 0 31 34 1 1 0 0 0 32 35 1 0 0 0 0 33 36 2 0 0 0 0 33 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.39
Volume:	584.603
LogP:	7.967
LogD:	4.424
LogS:	-2.921
# Rotatable Bonds:	23
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.079
Synthetic Accessibility Score:	4.018
Fsp3:	0.697
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.199
MDCK Permeability:	3.194059900124557e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.702
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	103.2903060913086%
Volume Distribution (VD):	1.985
Pgp-substrate:	0.5481052398681641%

ADMET: Metabolism

CYP1A2-inhibitor:	0.125
CYP1A2-substrate:	0.158
CYP2C19-inhibitor:	0.799
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.391
CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.466
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.525
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	4.51
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.862
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.975
Carcinogencity:	0.116
Eye Corrosion:	0.179
Eye Irritation:	0.938
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC470965

Natural Product ID:	NPC470965
*Common Name:**	(-)-Petrosynoic Acid D
IUPAC Name:	(4Z,16E,29E,31R)-15,31-dihydroxytritriaconta-4,16,29-trien-2,32-diynoic acid
Synonyms:	(-)-Petrosynoic Acid D
Standard InCHIKey:	WMKMNGSQNVMJIZ-SSDIRBQOSA-N
Standard InCHI:	InChI=1S/C33H52O4/c1-2-31(34)27-23-19-15-11-7-4-3-5-8-12-16-20-24-28-32(35)29-25-21-17-13-9-6-10-14-18-22-26-30-33(36)37/h1,18,22-24,27-28,31-32,34-35H,3-17,19-21,25,29H2,(H,36,37)/b22-18-,27-23+,28-24+/t31-,32?/m0/s1
SMILES:	C#C[C@@H](/C=C/CCCCCCCCCCC/C=C/C(CCCCCCCCC/C=CC#CC(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333787
PubChem CID:	71659021
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002950] Very long-chain fatty acids

*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
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	(15-25 m depth) off Komun Island, Korea	1995-JUL	PMID[10217707]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346968]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170665]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754614]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	1996	PMID[18327911]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Miyako sea-knoll, southwestern Japan (2525.64' N, 12542.48' E), at a depth of 415 m	2009-OCT	PMID[21534590]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	American Samoa	n.a.	PMID[23368996]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26821210]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917297]

☑ 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	4
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1383	Cell Line	A2058	Homo sapiens	IC50	=	8100.0	nM	PMID[541925]
NPT1383	Cell Line	A2058	Homo sapiens	Ratio IC50	=	0.0	n.a.	PMID[541925]
NPT4490	Cell Line	IMR-90	Homo sapiens	IC50	=	200.0	nM	PMID[541925]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[541925]

☑ 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 NPC470965 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	173
0.1-0.2	2831
0.2-0.3	15319
0.3-0.4	14302
0.4-0.5	7116
0.5-0.6	2301
0.6-0.7	474
0.7-0.8	123
0.8-0.85	21
0.85-0.9	30
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC475984
0.9138	High Similarity	NPC48968
0.9138	High Similarity	NPC594
0.9138	High Similarity	NPC470970
0.9016	High Similarity	NPC29697
0.8966	High Similarity	NPC473847
0.8966	High Similarity	NPC470967
0.8966	High Similarity	NPC470966
0.8966	High Similarity	NPC475384
0.8966	High Similarity	NPC477661
0.8966	High Similarity	NPC311648
0.8966	High Similarity	NPC470964
0.8966	High Similarity	NPC470969
0.8966	High Similarity	NPC161838
0.8966	High Similarity	NPC470968
0.8966	High Similarity	NPC471960
0.8852	High Similarity	NPC66460
0.8852	High Similarity	NPC271282
0.8852	High Similarity	NPC325929
0.8793	High Similarity	NPC146551
0.8793	High Similarity	NPC474513
0.8793	High Similarity	NPC473910
0.8793	High Similarity	NPC475353
0.8793	High Similarity	NPC473896
0.8793	High Similarity	NPC470963
0.8793	High Similarity	NPC473721
0.8793	High Similarity	NPC152668
0.8793	High Similarity	NPC473735
0.8793	High Similarity	NPC473725
0.8793	High Similarity	NPC477725
0.8793	High Similarity	NPC477726
0.8621	High Similarity	NPC473532
0.8448	Intermediate Similarity	NPC26102
0.8448	Intermediate Similarity	NPC477724
0.8448	Intermediate Similarity	NPC187361
0.8305	Intermediate Similarity	NPC256209
0.8305	Intermediate Similarity	NPC48058
0.8305	Intermediate Similarity	NPC49059
0.8281	Intermediate Similarity	NPC470320
0.8281	Intermediate Similarity	NPC226592
0.8254	Intermediate Similarity	NPC477829
0.8103	Intermediate Similarity	NPC129263
0.8103	Intermediate Similarity	NPC197272
0.8103	Intermediate Similarity	NPC55383
0.8103	Intermediate Similarity	NPC9273
0.8103	Intermediate Similarity	NPC256656
0.8103	Intermediate Similarity	NPC165447
0.8103	Intermediate Similarity	NPC224148
0.8103	Intermediate Similarity	NPC170776
0.8103	Intermediate Similarity	NPC294278
0.8103	Intermediate Similarity	NPC477723
0.8103	Intermediate Similarity	NPC329608
0.8103	Intermediate Similarity	NPC89824
0.8103	Intermediate Similarity	NPC475477
0.8103	Intermediate Similarity	NPC76198
0.8103	Intermediate Similarity	NPC471959
0.8095	Intermediate Similarity	NPC471278
0.7937	Intermediate Similarity	NPC474267
0.7931	Intermediate Similarity	NPC477727
0.7931	Intermediate Similarity	NPC471281
0.7931	Intermediate Similarity	NPC199286
0.791	Intermediate Similarity	NPC473752
0.791	Intermediate Similarity	NPC26500
0.791	Intermediate Similarity	NPC99619
0.7879	Intermediate Similarity	NPC245947
0.7879	Intermediate Similarity	NPC255863
0.7879	Intermediate Similarity	NPC136164
0.7833	Intermediate Similarity	NPC34577
0.7812	Intermediate Similarity	NPC327112
0.7797	Intermediate Similarity	NPC151782
0.7759	Intermediate Similarity	NPC471280
0.7759	Intermediate Similarity	NPC125122
0.7759	Intermediate Similarity	NPC471275
0.7759	Intermediate Similarity	NPC471276
0.7705	Intermediate Similarity	NPC110732
0.7692	Intermediate Similarity	NPC321838
0.7681	Intermediate Similarity	NPC470436
0.7656	Intermediate Similarity	NPC473652
0.7627	Intermediate Similarity	NPC474642
0.7627	Intermediate Similarity	NPC72699
0.7627	Intermediate Similarity	NPC473913
0.7627	Intermediate Similarity	NPC249670
0.7619	Intermediate Similarity	NPC212730
0.7619	Intermediate Similarity	NPC471279
0.7619	Intermediate Similarity	NPC472445
0.7619	Intermediate Similarity	NPC471277
0.7619	Intermediate Similarity	NPC44542
0.7619	Intermediate Similarity	NPC265551
0.7612	Intermediate Similarity	NPC318420
0.7612	Intermediate Similarity	NPC326268
0.7581	Intermediate Similarity	NPC471239
0.7538	Intermediate Similarity	NPC299730
0.7538	Intermediate Similarity	NPC328311
0.7538	Intermediate Similarity	NPC243532
0.75	Intermediate Similarity	NPC469373
0.7458	Intermediate Similarity	NPC85079
0.7458	Intermediate Similarity	NPC31194
0.7458	Intermediate Similarity	NPC153538
0.7458	Intermediate Similarity	NPC248884
0.7429	Intermediate Similarity	NPC143396
0.7424	Intermediate Similarity	NPC168407
0.7424	Intermediate Similarity	NPC201939
0.7414	Intermediate Similarity	NPC35141
0.7414	Intermediate Similarity	NPC124183
0.7385	Intermediate Similarity	NPC222852
0.7361	Intermediate Similarity	NPC470435
0.7361	Intermediate Similarity	NPC329890
0.7344	Intermediate Similarity	NPC193975
0.7324	Intermediate Similarity	NPC4299
0.7302	Intermediate Similarity	NPC52264
0.7302	Intermediate Similarity	NPC54766
0.7286	Intermediate Similarity	NPC324981
0.7286	Intermediate Similarity	NPC141481
0.7286	Intermediate Similarity	NPC48218
0.7286	Intermediate Similarity	NPC473559
0.726	Intermediate Similarity	NPC227396
0.7258	Intermediate Similarity	NPC474496
0.7246	Intermediate Similarity	NPC328653
0.7213	Intermediate Similarity	NPC59408
0.7213	Intermediate Similarity	NPC474495
0.7213	Intermediate Similarity	NPC473672
0.7213	Intermediate Similarity	NPC71053
0.7213	Intermediate Similarity	NPC93639
0.7188	Intermediate Similarity	NPC187777
0.7188	Intermediate Similarity	NPC324224
0.7188	Intermediate Similarity	NPC179764
0.7188	Intermediate Similarity	NPC472808
0.7183	Intermediate Similarity	NPC236208
0.7183	Intermediate Similarity	NPC101622
0.7164	Intermediate Similarity	NPC328776
0.7164	Intermediate Similarity	NPC320305
0.7164	Intermediate Similarity	NPC26810
0.7164	Intermediate Similarity	NPC113293
0.7162	Intermediate Similarity	NPC285840
0.7162	Intermediate Similarity	NPC327041
0.7143	Intermediate Similarity	NPC271921
0.7143	Intermediate Similarity	NPC330426
0.7143	Intermediate Similarity	NPC475443
0.7143	Intermediate Similarity	NPC137538
0.7143	Intermediate Similarity	NPC473829
0.7143	Intermediate Similarity	NPC49863
0.7143	Intermediate Similarity	NPC148192
0.7143	Intermediate Similarity	NPC22101
0.7143	Intermediate Similarity	NPC104537
0.7143	Intermediate Similarity	NPC127091
0.7123	Intermediate Similarity	NPC477085
0.7123	Intermediate Similarity	NPC325627
0.7123	Intermediate Similarity	NPC185186
0.7123	Intermediate Similarity	NPC327383
0.7123	Intermediate Similarity	NPC329914
0.7121	Intermediate Similarity	NPC322186
0.7121	Intermediate Similarity	NPC329249
0.7121	Intermediate Similarity	NPC318306
0.7121	Intermediate Similarity	NPC322002
0.7119	Intermediate Similarity	NPC19834
0.7119	Intermediate Similarity	NPC55063
0.7101	Intermediate Similarity	NPC323477
0.7101	Intermediate Similarity	NPC323045
0.7101	Intermediate Similarity	NPC317881
0.7083	Intermediate Similarity	NPC476037
0.7083	Intermediate Similarity	NPC476660
0.7077	Intermediate Similarity	NPC323436
0.7069	Intermediate Similarity	NPC101616
0.7067	Intermediate Similarity	NPC279537
0.7067	Intermediate Similarity	NPC188860
0.7049	Intermediate Similarity	NPC328784
0.7049	Intermediate Similarity	NPC291437
0.7031	Intermediate Similarity	NPC317899
0.7031	Intermediate Similarity	NPC473863
0.7031	Intermediate Similarity	NPC274290
0.7031	Intermediate Similarity	NPC474644
0.7013	Intermediate Similarity	NPC470149
0.7013	Intermediate Similarity	NPC470148
0.7	Intermediate Similarity	NPC146811
0.7	Intermediate Similarity	NPC476656
0.7	Intermediate Similarity	NPC476659
0.6986	Remote Similarity	NPC477087
0.6986	Remote Similarity	NPC477086
0.6974	Remote Similarity	NPC233071
0.697	Remote Similarity	NPC34416
0.6957	Remote Similarity	NPC476658
0.6957	Remote Similarity	NPC68343
0.6957	Remote Similarity	NPC328089
0.6949	Remote Similarity	NPC269074
0.6949	Remote Similarity	NPC76976
0.6944	Remote Similarity	NPC473772
0.6933	Remote Similarity	NPC260396
0.6923	Remote Similarity	NPC474643
0.6923	Remote Similarity	NPC133226
0.6923	Remote Similarity	NPC473865
0.6923	Remote Similarity	NPC477201
0.6923	Remote Similarity	NPC470147
0.6901	Remote Similarity	NPC193029
0.6901	Remote Similarity	NPC478097
0.6901	Remote Similarity	NPC473357
0.6901	Remote Similarity	NPC25298
0.6885	Remote Similarity	NPC207815
0.6885	Remote Similarity	NPC302310
0.6883	Remote Similarity	NPC192006
0.6883	Remote Similarity	NPC248775

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 NPC470965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	3317
0.2-0.3	3917
0.3-0.4	1407
0.4-0.5	270
0.5-0.6	74
0.6-0.7	28
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
0.7812	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3197	Phase 1
0.7143	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5331	Approved
0.7089	Intermediate Similarity	NPD5332	Approved
0.6883	Remote Similarity	NPD4271	Approved
0.6883	Remote Similarity	NPD4268	Approved
0.6875	Remote Similarity	NPD3196	Approved
0.6875	Remote Similarity	NPD3194	Approved
0.6875	Remote Similarity	NPD4266	Approved
0.6875	Remote Similarity	NPD3195	Phase 2
0.6719	Remote Similarity	NPD3172	Approved
0.6709	Remote Similarity	NPD4821	Approved
0.6709	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4820	Approved
0.6709	Remote Similarity	NPD4819	Approved
0.6709	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4790	Discontinued
0.6543	Remote Similarity	NPD4269	Approved
0.6543	Remote Similarity	NPD4270	Approved
0.6506	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4252	Approved
0.6463	Remote Similarity	NPD5362	Discontinued
0.6463	Remote Similarity	NPD7154	Phase 3
0.6406	Remote Similarity	NPD29	Approved
0.6406	Remote Similarity	NPD28	Approved
0.6393	Remote Similarity	NPD4265	Approved
0.6393	Remote Similarity	NPD39	Approved
0.6349	Remote Similarity	NPD3173	Approved
0.631	Remote Similarity	NPD5363	Approved
0.6235	Remote Similarity	NPD5786	Approved
0.6232	Remote Similarity	NPD6109	Phase 1
0.619	Remote Similarity	NPD622	Approved
0.6163	Remote Similarity	NPD4251	Approved
0.6163	Remote Similarity	NPD4250	Approved
0.6129	Remote Similarity	NPD4222	Approved
0.6111	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD5368	Approved
0.6067	Remote Similarity	NPD7983	Approved
0.6066	Remote Similarity	NPD5326	Phase 3
0.6047	Remote Similarity	NPD4249	Approved
0.6024	Remote Similarity	NPD5369	Approved
0.6023	Remote Similarity	NPD5370	Suspended
0.5955	Remote Similarity	NPD5785	Approved
0.5955	Remote Similarity	NPD7838	Discovery
0.5952	Remote Similarity	NPD6435	Approved
0.5946	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5343	Approved
0.5926	Remote Similarity	NPD4756	Discovery
0.5889	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD8264	Approved
0.5873	Remote Similarity	NPD3174	Discontinued
0.5846	Remote Similarity	NPD4220	Pre-registration
0.5824	Remote Similarity	NPD5779	Approved
0.5824	Remote Similarity	NPD5778	Approved
0.5814	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7839	Suspended
0.5797	Remote Similarity	NPD342	Phase 1
0.5769	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD368	Approved
0.5714	Remote Similarity	NPD6097	Approved
0.5714	Remote Similarity	NPD6096	Approved
0.5714	Remote Similarity	NPD7637	Suspended
0.5684	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD8039	Approved
0.5672	Remote Similarity	NPD6927	Phase 3
0.5667	Remote Similarity	NPD6051	Approved
0.5663	Remote Similarity	NPD3732	Approved
0.5638	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD7750	Discontinued
0.5604	Remote Similarity	NPD46	Approved
0.5604	Remote Similarity	NPD6698	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