NPASS Compound

Structure

NPC475984 OpenBabel07101719152D 35 34 0 0 1 0 0 0 0 0999 V2000 15.5885 14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 14.5000 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 5.1962 2.0000 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 2.5000 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 10.3923 12.0000 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 10.3923 13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 11.5000 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 11.2583 13.5000 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 9.5263 10.5000 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 11.2583 14.5000 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 9.5263 9.5000 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 12.1244 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 5.5000 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 1.7321 -2.0000 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 7.7942 6.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 15.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6603 7.0000 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 13.8564 16.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 6.5000 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 -0.0000 -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 29 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 12 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 14 1 0 0 0 0 10 13 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 3 0 0 0 0 16 20 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 25 2 0 0 0 0 22 26 1 0 0 0 0 23 27 2 0 0 0 0 24 28 3 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 27 30 1 0 0 0 0 28 31 1 0 0 0 0 29 32 1 1 0 0 0 30 33 1 0 0 0 0 31 34 2 0 0 0 0 31 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.32
Volume:	553.528
LogP:	6.965
LogD:	2.924
LogS:	-3.255
# Rotatable Bonds:	19
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	4.282
Fsp3:	0.581
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.582
MDCK Permeability:	4.2394061892991886e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.936
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	102.4985580444336%
Volume Distribution (VD):	0.969
Pgp-substrate:	0.3452489972114563%

ADMET: Metabolism

CYP1A2-inhibitor:	0.489
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.784
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.684
CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.844
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.68
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	2.419
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.873
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.79
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.979
Carcinogencity:	0.155
Eye Corrosion:	0.332
Eye Irritation:	0.946
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC475984

Natural Product ID:	NPC475984
*Common Name:**	Corticatic Acid D
IUPAC Name:	(4Z,18E,27E,29R)-17,29-dihydroxyhentriaconta-4,18,27-trien-2,20,30-triynoic acid
Synonyms:	Corticatic Acid D
Standard InCHIKey:	BUDYGGALOGHSBM-BINRPSKSSA-N
Standard InCHI:	InChI=1S/C31H44O4/c1-2-29(32)25-21-17-13-10-8-11-15-19-23-27-30(33)26-22-18-14-9-6-4-3-5-7-12-16-20-24-28-31(34)35/h1,16,20-21,23,25,27,29-30,32-33H,3-14,17-18,22,26H2,(H,34,35)/b20-16-,25-21+,27-23+/t29-,30?/m0/s1
SMILES:	C#C[C@@H](/C=C/CCCCCC#C/C=C/C(CCCCCCCCCCC/C=CC#CC(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520492
PubChem CID:	21776568
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
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350165]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	Okinawan, Japan	n.a.	PMID[14695804]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332859]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17407351]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25987373]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7807132]
NPO24364	Petrosia corticata	Species	Petrosiidae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	3300.0	nM	PMID[500712]

☑ 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 NPC475984 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	171
0.1-0.2	2761
0.2-0.3	15025
0.3-0.4	14695
0.4-0.5	6956
0.5-0.6	2412
0.6-0.7	477
0.7-0.8	138
0.8-0.85	17
0.85-0.9	38
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC470965
0.9167	High Similarity	NPC29697
0.9	High Similarity	NPC325929
0.9	High Similarity	NPC66460
0.9	High Similarity	NPC271282
0.8966	High Similarity	NPC48968
0.8966	High Similarity	NPC594
0.8966	High Similarity	NPC470970
0.8947	High Similarity	NPC477725
0.8947	High Similarity	NPC474513
0.8947	High Similarity	NPC477726
0.8947	High Similarity	NPC146551
0.8947	High Similarity	NPC470963
0.8793	High Similarity	NPC470967
0.8793	High Similarity	NPC470969
0.8793	High Similarity	NPC477661
0.8793	High Similarity	NPC161838
0.8793	High Similarity	NPC311648
0.8793	High Similarity	NPC470964
0.8793	High Similarity	NPC471960
0.8793	High Similarity	NPC470966
0.8793	High Similarity	NPC473847
0.8793	High Similarity	NPC470968
0.8793	High Similarity	NPC475384
0.8621	High Similarity	NPC473725
0.8621	High Similarity	NPC152668
0.8621	High Similarity	NPC473910
0.8621	High Similarity	NPC473721
0.8621	High Similarity	NPC473735
0.8621	High Similarity	NPC475353
0.8621	High Similarity	NPC473896
0.8448	Intermediate Similarity	NPC49059
0.8448	Intermediate Similarity	NPC473532
0.8448	Intermediate Similarity	NPC256209
0.8413	Intermediate Similarity	NPC226592
0.8413	Intermediate Similarity	NPC470320
0.8387	Intermediate Similarity	NPC477829
0.8276	Intermediate Similarity	NPC187361
0.8276	Intermediate Similarity	NPC26102
0.8276	Intermediate Similarity	NPC477724
0.8246	Intermediate Similarity	NPC55383
0.8246	Intermediate Similarity	NPC129263
0.8226	Intermediate Similarity	NPC471278
0.8136	Intermediate Similarity	NPC48058
0.807	Intermediate Similarity	NPC199286
0.807	Intermediate Similarity	NPC477727
0.807	Intermediate Similarity	NPC471281
0.8065	Intermediate Similarity	NPC474267
0.803	Intermediate Similarity	NPC26500
0.803	Intermediate Similarity	NPC99619
0.8	Intermediate Similarity	NPC255863
0.8	Intermediate Similarity	NPC136164
0.8	Intermediate Similarity	NPC245947
0.7966	Intermediate Similarity	NPC34577
0.7937	Intermediate Similarity	NPC327112
0.7931	Intermediate Similarity	NPC9273
0.7931	Intermediate Similarity	NPC170776
0.7931	Intermediate Similarity	NPC256656
0.7931	Intermediate Similarity	NPC471959
0.7931	Intermediate Similarity	NPC224148
0.7931	Intermediate Similarity	NPC197272
0.7931	Intermediate Similarity	NPC475477
0.7931	Intermediate Similarity	NPC89824
0.7931	Intermediate Similarity	NPC477723
0.7931	Intermediate Similarity	NPC76198
0.7931	Intermediate Similarity	NPC294278
0.7931	Intermediate Similarity	NPC151782
0.7931	Intermediate Similarity	NPC165447
0.7931	Intermediate Similarity	NPC329608
0.7895	Intermediate Similarity	NPC125122
0.7895	Intermediate Similarity	NPC471275
0.7895	Intermediate Similarity	NPC471276
0.7895	Intermediate Similarity	NPC471280
0.7833	Intermediate Similarity	NPC110732
0.7812	Intermediate Similarity	NPC321838
0.7794	Intermediate Similarity	NPC470436
0.7761	Intermediate Similarity	NPC473752
0.7759	Intermediate Similarity	NPC474642
0.7759	Intermediate Similarity	NPC72699
0.7759	Intermediate Similarity	NPC473913
0.7759	Intermediate Similarity	NPC249670
0.7742	Intermediate Similarity	NPC44542
0.7742	Intermediate Similarity	NPC212730
0.7742	Intermediate Similarity	NPC265551
0.7742	Intermediate Similarity	NPC471279
0.7742	Intermediate Similarity	NPC472445
0.7742	Intermediate Similarity	NPC471277
0.7727	Intermediate Similarity	NPC326268
0.7727	Intermediate Similarity	NPC318420
0.7705	Intermediate Similarity	NPC471239
0.7656	Intermediate Similarity	NPC243532
0.7656	Intermediate Similarity	NPC328311
0.7656	Intermediate Similarity	NPC299730
0.7619	Intermediate Similarity	NPC469373
0.7586	Intermediate Similarity	NPC153538
0.7586	Intermediate Similarity	NPC85079
0.7586	Intermediate Similarity	NPC248884
0.7586	Intermediate Similarity	NPC31194
0.7544	Intermediate Similarity	NPC124183
0.7544	Intermediate Similarity	NPC35141
0.7538	Intermediate Similarity	NPC201939
0.7536	Intermediate Similarity	NPC143396
0.75	Intermediate Similarity	NPC222852
0.75	Intermediate Similarity	NPC473652
0.7465	Intermediate Similarity	NPC470435
0.7465	Intermediate Similarity	NPC329890
0.746	Intermediate Similarity	NPC193975
0.7429	Intermediate Similarity	NPC4299
0.7419	Intermediate Similarity	NPC54766
0.7419	Intermediate Similarity	NPC52264
0.7377	Intermediate Similarity	NPC474496
0.7361	Intermediate Similarity	NPC227396
0.7353	Intermediate Similarity	NPC328653
0.7333	Intermediate Similarity	NPC473672
0.7333	Intermediate Similarity	NPC93639
0.7333	Intermediate Similarity	NPC59408
0.7333	Intermediate Similarity	NPC474495
0.7333	Intermediate Similarity	NPC71053
0.7302	Intermediate Similarity	NPC324224
0.7302	Intermediate Similarity	NPC179764
0.7302	Intermediate Similarity	NPC472808
0.7302	Intermediate Similarity	NPC187777
0.7286	Intermediate Similarity	NPC101622
0.7286	Intermediate Similarity	NPC236208
0.7273	Intermediate Similarity	NPC113293
0.7273	Intermediate Similarity	NPC26810
0.7273	Intermediate Similarity	NPC168407
0.7273	Intermediate Similarity	NPC320305
0.7273	Intermediate Similarity	NPC328776
0.7258	Intermediate Similarity	NPC137538
0.7246	Intermediate Similarity	NPC49863
0.7246	Intermediate Similarity	NPC104537
0.7246	Intermediate Similarity	NPC148192
0.7246	Intermediate Similarity	NPC271921
0.7246	Intermediate Similarity	NPC22101
0.7246	Intermediate Similarity	NPC127091
0.7246	Intermediate Similarity	NPC330426
0.7241	Intermediate Similarity	NPC19834
0.7241	Intermediate Similarity	NPC55063
0.7231	Intermediate Similarity	NPC329249
0.7231	Intermediate Similarity	NPC318306
0.7231	Intermediate Similarity	NPC322186
0.7231	Intermediate Similarity	NPC322002
0.7222	Intermediate Similarity	NPC477085
0.7222	Intermediate Similarity	NPC327383
0.7222	Intermediate Similarity	NPC325627
0.7222	Intermediate Similarity	NPC185186
0.7222	Intermediate Similarity	NPC329914
0.7206	Intermediate Similarity	NPC317881
0.7206	Intermediate Similarity	NPC323045
0.7206	Intermediate Similarity	NPC323477
0.7193	Intermediate Similarity	NPC101616
0.7188	Intermediate Similarity	NPC323436
0.7183	Intermediate Similarity	NPC476037
0.7167	Intermediate Similarity	NPC328784
0.7167	Intermediate Similarity	NPC291437
0.7162	Intermediate Similarity	NPC188860
0.7162	Intermediate Similarity	NPC279537
0.7143	Intermediate Similarity	NPC317899
0.7143	Intermediate Similarity	NPC473863
0.7143	Intermediate Similarity	NPC474644
0.7143	Intermediate Similarity	NPC274290
0.7143	Intermediate Similarity	NPC473559
0.7143	Intermediate Similarity	NPC48218
0.7143	Intermediate Similarity	NPC324981
0.7143	Intermediate Similarity	NPC141481
0.7101	Intermediate Similarity	NPC146811
0.7083	Intermediate Similarity	NPC477087
0.7083	Intermediate Similarity	NPC477086
0.7077	Intermediate Similarity	NPC34416
0.7069	Intermediate Similarity	NPC76976
0.7069	Intermediate Similarity	NPC269074
0.7067	Intermediate Similarity	NPC233071
0.7059	Intermediate Similarity	NPC328089
0.7059	Intermediate Similarity	NPC68343
0.7031	Intermediate Similarity	NPC474643
0.7031	Intermediate Similarity	NPC473865
0.7031	Intermediate Similarity	NPC477201
0.7027	Intermediate Similarity	NPC327041
0.7027	Intermediate Similarity	NPC285840
0.7027	Intermediate Similarity	NPC260396
0.7	Intermediate Similarity	NPC475443
0.7	Intermediate Similarity	NPC25298
0.7	Intermediate Similarity	NPC207815
0.7	Intermediate Similarity	NPC302310
0.7	Intermediate Similarity	NPC478097
0.7	Intermediate Similarity	NPC473829
0.6984	Remote Similarity	NPC424
0.6984	Remote Similarity	NPC290563
0.6984	Remote Similarity	NPC6095
0.6984	Remote Similarity	NPC32467
0.6984	Remote Similarity	NPC87564
0.6984	Remote Similarity	NPC85813
0.6984	Remote Similarity	NPC25417
0.6984	Remote Similarity	NPC281972
0.6984	Remote Similarity	NPC261831
0.6984	Remote Similarity	NPC154245
0.6984	Remote Similarity	NPC88966
0.6974	Remote Similarity	NPC323249
0.6974	Remote Similarity	NPC27949

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 NPC475984 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	3249
0.2-0.3	3932
0.3-0.4	1443
0.4-0.5	288
0.5-0.6	73
0.6-0.7	28
0.7-0.8	3
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
0.7937	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3197	Phase 1
0.7246	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5331	Approved
0.7179	Intermediate Similarity	NPD5332	Approved
0.6984	Remote Similarity	NPD3195	Phase 2
0.6984	Remote Similarity	NPD4266	Approved
0.6984	Remote Similarity	NPD3194	Approved
0.6984	Remote Similarity	NPD3196	Approved
0.6974	Remote Similarity	NPD4271	Approved
0.6974	Remote Similarity	NPD4268	Approved
0.6825	Remote Similarity	NPD3172	Approved
0.6795	Remote Similarity	NPD4819	Approved
0.6795	Remote Similarity	NPD4821	Approved
0.6795	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4820	Approved
0.6795	Remote Similarity	NPD4822	Approved
0.6753	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4790	Discontinued
0.6625	Remote Similarity	NPD4270	Approved
0.6625	Remote Similarity	NPD4269	Approved
0.6585	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4252	Approved
0.6543	Remote Similarity	NPD5362	Discontinued
0.6543	Remote Similarity	NPD7154	Phase 3
0.6508	Remote Similarity	NPD28	Approved
0.6508	Remote Similarity	NPD29	Approved
0.65	Remote Similarity	NPD4265	Approved
0.65	Remote Similarity	NPD39	Approved
0.6452	Remote Similarity	NPD3173	Approved
0.6386	Remote Similarity	NPD5363	Approved
0.6324	Remote Similarity	NPD6109	Phase 1
0.631	Remote Similarity	NPD5786	Approved
0.629	Remote Similarity	NPD622	Approved
0.6235	Remote Similarity	NPD4251	Approved
0.6235	Remote Similarity	NPD4250	Approved
0.623	Remote Similarity	NPD4222	Approved
0.6197	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD5368	Approved
0.6167	Remote Similarity	NPD5326	Phase 3
0.6118	Remote Similarity	NPD4249	Approved
0.6098	Remote Similarity	NPD5369	Approved
0.6092	Remote Similarity	NPD5370	Suspended
0.6032	Remote Similarity	NPD5343	Approved
0.6027	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD6435	Approved
0.6023	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD4756	Discovery
0.5968	Remote Similarity	NPD3174	Discontinued
0.5955	Remote Similarity	NPD7983	Approved
0.5955	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4220	Pre-registration
0.5889	Remote Similarity	NPD5778	Approved
0.5889	Remote Similarity	NPD5779	Approved
0.5882	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD342	Phase 1
0.5844	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD7838	Discovery
0.5833	Remote Similarity	NPD368	Approved
0.5806	Remote Similarity	NPD6097	Approved
0.5806	Remote Similarity	NPD6096	Approved
0.5778	Remote Similarity	NPD7637	Suspended
0.5758	Remote Similarity	NPD6927	Phase 3
0.575	Remote Similarity	NPD8264	Approved
0.5732	Remote Similarity	NPD3732	Approved
0.573	Remote Similarity	NPD6051	Approved
0.5699	Remote Similarity	NPD7839	Suspended
0.5699	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6698	Approved
0.5667	Remote Similarity	NPD46	Approved
0.5634	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD4191	Approved
0.5616	Remote Similarity	NPD4194	Approved
0.5616	Remote Similarity	NPD4192	Approved
0.5616	Remote Similarity	NPD4193	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