NPASS Compound

Structure

NPC143396 OpenBabel07101718222D 22 21 0 0 1 0 0 0 0 0999 V2000 14.7224 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 1.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 1.5000 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 8.6603 1.0000 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 12.1244 1.0000 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 7.7942 1.5000 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 12.9904 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 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 12.9904 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 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 1 0 0 0 0 2 16 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 9 1 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 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 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 1 0 0 0 17 20 2 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.2
Volume:	341.863
LogP:	2.498
LogD:	1.5
LogS:	-3.662
# Rotatable Bonds:	13
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.308
Synthetic Accessibility Score:	3.212
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.991
MDCK Permeability:	4.776975038112141e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	86.10774993896484%
Volume Distribution (VD):	0.32
Pgp-substrate:	11.121334075927734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.349
CYP1A2-substrate:	0.148
CYP2C19-inhibitor:	0.121
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.163
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.117
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	2.807
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.392
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.603
Skin Sensitization:	0.834
Carcinogencity:	0.681
Eye Corrosion:	0.175
Eye Irritation:	0.817
Respiratory Toxicity:	0.791

Download Data

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

Natural Product: NPC143396

Natural Product ID:	NPC143396
*Common Name:**	Corchorifatty Acid B
IUPAC Name:	(10E,12E,14E,16S)-16-hydroxy-9-oxooctadeca-10,12,14-trienoic acid
Synonyms:	Corchorifatty Acid B
Standard InCHIKey:	KLFMLBSZQZVKDC-JMJILCHISA-N
Standard InCHI:	InChI=1S/C18H28O4/c1-2-16(19)12-8-6-7-10-14-17(20)13-9-4-3-5-11-15-18(21)22/h6-8,10,12,14,16,19H,2-5,9,11,13,15H2,1H3,(H,21,22)/b7-6+,12-8+,14-10+/t16-/m0/s1
SMILES:	CC[C@@H](/C=C/C=C/C=C/C(=O)CCCCCCCC(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668472
PubChem CID:	22956671
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids 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
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10896056]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374970]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17338565]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21273070]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22066578]
NPO26913	Isodon excisus	Species	Lamiaceae	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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	40000.0	nM	PMID[543289]

☑ 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 NPC143396 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	168
0.1-0.2	1408
0.2-0.3	7390
0.3-0.4	16708
0.4-0.5	10016
0.5-0.6	4874
0.6-0.7	1791
0.7-0.8	300
0.8-0.85	23
0.85-0.9	14
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.913	High Similarity	NPC227396
0.9077	High Similarity	NPC255863
0.9077	High Similarity	NPC245947
0.9077	High Similarity	NPC136164
0.8906	High Similarity	NPC40082
0.8824	High Similarity	NPC236208
0.8788	High Similarity	NPC318420
0.8788	High Similarity	NPC326268
0.875	High Similarity	NPC122521
0.875	High Similarity	NPC251042
0.875	High Similarity	NPC174447
0.8636	High Similarity	NPC470320
0.8592	High Similarity	NPC474321
0.8529	High Similarity	NPC26500
0.8529	High Similarity	NPC99619
0.8472	Intermediate Similarity	NPC260396
0.8462	Intermediate Similarity	NPC327112
0.8438	Intermediate Similarity	NPC34416
0.8378	Intermediate Similarity	NPC192006
0.8358	Intermediate Similarity	NPC226592
0.8308	Intermediate Similarity	NPC106851
0.8308	Intermediate Similarity	NPC274927
0.8194	Intermediate Similarity	NPC325627
0.8182	Intermediate Similarity	NPC235242
0.8182	Intermediate Similarity	NPC328311
0.8182	Intermediate Similarity	NPC243532
0.8125	Intermediate Similarity	NPC472808
0.8125	Intermediate Similarity	NPC325977
0.8125	Intermediate Similarity	NPC324224
0.806	Intermediate Similarity	NPC477829
0.806	Intermediate Similarity	NPC201939
0.8056	Intermediate Similarity	NPC319163
0.8056	Intermediate Similarity	NPC67076
0.8	Intermediate Similarity	NPC49863
0.7971	Intermediate Similarity	NPC323477
0.7971	Intermediate Similarity	NPC317881
0.7971	Intermediate Similarity	NPC323045
0.7945	Intermediate Similarity	NPC329890
0.7917	Intermediate Similarity	NPC476660
0.791	Intermediate Similarity	NPC143857
0.791	Intermediate Similarity	NPC229252
0.7895	Intermediate Similarity	NPC182292
0.7867	Intermediate Similarity	NPC279537
0.7857	Intermediate Similarity	NPC142423
0.7857	Intermediate Similarity	NPC308294
0.7857	Intermediate Similarity	NPC328653
0.7846	Intermediate Similarity	NPC477201
0.7846	Intermediate Similarity	NPC18951
0.7812	Intermediate Similarity	NPC322461
0.7808	Intermediate Similarity	NPC288667
0.7794	Intermediate Similarity	NPC321838
0.7778	Intermediate Similarity	NPC473772
0.7761	Intermediate Similarity	NPC322002
0.7761	Intermediate Similarity	NPC329550
0.7761	Intermediate Similarity	NPC318306
0.7761	Intermediate Similarity	NPC329249
0.7746	Intermediate Similarity	NPC148192
0.7746	Intermediate Similarity	NPC271921
0.7746	Intermediate Similarity	NPC104537
0.7746	Intermediate Similarity	NPC127091
0.7746	Intermediate Similarity	NPC22101
0.7746	Intermediate Similarity	NPC330426
0.7727	Intermediate Similarity	NPC225929
0.7714	Intermediate Similarity	NPC320642
0.7703	Intermediate Similarity	NPC329914
0.7681	Intermediate Similarity	NPC29697
0.7671	Intermediate Similarity	NPC318766
0.7671	Intermediate Similarity	NPC476037
0.7671	Intermediate Similarity	NPC42526
0.7656	Intermediate Similarity	NPC36061
0.7656	Intermediate Similarity	NPC139029
0.7656	Intermediate Similarity	NPC1813
0.7656	Intermediate Similarity	NPC294548
0.7654	Intermediate Similarity	NPC261380
0.7639	Intermediate Similarity	NPC473559
0.7639	Intermediate Similarity	NPC218477
0.7639	Intermediate Similarity	NPC141481
0.7639	Intermediate Similarity	NPC48218
0.7639	Intermediate Similarity	NPC324981
0.7632	Intermediate Similarity	NPC188860
0.7606	Intermediate Similarity	NPC146811
0.7571	Intermediate Similarity	NPC328089
0.7571	Intermediate Similarity	NPC68343
0.7561	Intermediate Similarity	NPC315395
0.7561	Intermediate Similarity	NPC316426
0.7538	Intermediate Similarity	NPC25417
0.7538	Intermediate Similarity	NPC32467
0.7538	Intermediate Similarity	NPC261831
0.7538	Intermediate Similarity	NPC290563
0.7538	Intermediate Similarity	NPC424
0.7538	Intermediate Similarity	NPC88966
0.7538	Intermediate Similarity	NPC154245
0.7538	Intermediate Similarity	NPC281972
0.7538	Intermediate Similarity	NPC6095
0.7538	Intermediate Similarity	NPC87564
0.7538	Intermediate Similarity	NPC85813
0.7536	Intermediate Similarity	NPC113293
0.7536	Intermediate Similarity	NPC475984
0.7536	Intermediate Similarity	NPC66460
0.7536	Intermediate Similarity	NPC26810
0.7536	Intermediate Similarity	NPC325929
0.7536	Intermediate Similarity	NPC271282
0.7534	Intermediate Similarity	NPC475004
0.7534	Intermediate Similarity	NPC470436
0.7534	Intermediate Similarity	NPC475982
0.7532	Intermediate Similarity	NPC233071
0.75	Intermediate Similarity	NPC212598
0.75	Intermediate Similarity	NPC85772
0.75	Intermediate Similarity	NPC322186
0.75	Intermediate Similarity	NPC473829
0.75	Intermediate Similarity	NPC475443
0.75	Intermediate Similarity	NPC281245
0.7467	Intermediate Similarity	NPC284006
0.7467	Intermediate Similarity	NPC474705
0.7467	Intermediate Similarity	NPC326024
0.7465	Intermediate Similarity	NPC476657
0.7465	Intermediate Similarity	NPC296436
0.7465	Intermediate Similarity	NPC476655
0.7465	Intermediate Similarity	NPC176215
0.7465	Intermediate Similarity	NPC476654
0.7439	Intermediate Similarity	NPC28887
0.7439	Intermediate Similarity	NPC125290
0.7436	Intermediate Similarity	NPC93763
0.7436	Intermediate Similarity	NPC108816
0.7436	Intermediate Similarity	NPC231739
0.7432	Intermediate Similarity	NPC476012
0.7429	Intermediate Similarity	NPC470965
0.7424	Intermediate Similarity	NPC228473
0.7424	Intermediate Similarity	NPC52264
0.7424	Intermediate Similarity	NPC317899
0.7407	Intermediate Similarity	NPC253801
0.7407	Intermediate Similarity	NPC144415
0.7407	Intermediate Similarity	NPC16488
0.7403	Intermediate Similarity	NPC16279
0.7403	Intermediate Similarity	NPC205615
0.7403	Intermediate Similarity	NPC256640
0.7397	Intermediate Similarity	NPC474823
0.7397	Intermediate Similarity	NPC476614
0.7385	Intermediate Similarity	NPC321062
0.7385	Intermediate Similarity	NPC70387
0.7375	Intermediate Similarity	NPC47031
0.7368	Intermediate Similarity	NPC92558
0.7361	Intermediate Similarity	NPC476659
0.7361	Intermediate Similarity	NPC83965
0.7361	Intermediate Similarity	NPC476656
0.7349	Intermediate Similarity	NPC122502
0.7349	Intermediate Similarity	NPC234038
0.7349	Intermediate Similarity	NPC164393
0.7342	Intermediate Similarity	NPC164308
0.7342	Intermediate Similarity	NPC201225
0.7342	Intermediate Similarity	NPC1180
0.7333	Intermediate Similarity	NPC84038
0.7333	Intermediate Similarity	NPC320119
0.7333	Intermediate Similarity	NPC293114
0.7326	Intermediate Similarity	NPC142838
0.7313	Intermediate Similarity	NPC179764
0.7313	Intermediate Similarity	NPC187777
0.7308	Intermediate Similarity	NPC7563
0.7308	Intermediate Similarity	NPC471061
0.7308	Intermediate Similarity	NPC86917
0.7308	Intermediate Similarity	NPC116177
0.7308	Intermediate Similarity	NPC473536
0.7308	Intermediate Similarity	NPC320630
0.7297	Intermediate Similarity	NPC67608
0.7286	Intermediate Similarity	NPC168407
0.7286	Intermediate Similarity	NPC320305
0.7286	Intermediate Similarity	NPC328776
0.7284	Intermediate Similarity	NPC11332
0.7284	Intermediate Similarity	NPC73310
0.7284	Intermediate Similarity	NPC473780
0.7284	Intermediate Similarity	NPC131002
0.7284	Intermediate Similarity	NPC473529
0.7284	Intermediate Similarity	NPC475159
0.7284	Intermediate Similarity	NPC473712
0.7284	Intermediate Similarity	NPC329829
0.7284	Intermediate Similarity	NPC7414
0.7284	Intermediate Similarity	NPC145914
0.7284	Intermediate Similarity	NPC94875
0.7284	Intermediate Similarity	NPC180363
0.7284	Intermediate Similarity	NPC65930
0.7273	Intermediate Similarity	NPC137538
0.7273	Intermediate Similarity	NPC329826
0.7273	Intermediate Similarity	NPC469414
0.726	Intermediate Similarity	NPC122627
0.726	Intermediate Similarity	NPC25298
0.725	Intermediate Similarity	NPC271104
0.725	Intermediate Similarity	NPC115418
0.7241	Intermediate Similarity	NPC476049
0.7237	Intermediate Similarity	NPC185186
0.7237	Intermediate Similarity	NPC144419
0.7237	Intermediate Similarity	NPC327383
0.7237	Intermediate Similarity	NPC12815
0.7237	Intermediate Similarity	NPC215745
0.7237	Intermediate Similarity	NPC470435
0.7237	Intermediate Similarity	NPC275098
0.7237	Intermediate Similarity	NPC238948
0.7231	Intermediate Similarity	NPC92114
0.7229	Intermediate Similarity	NPC322529
0.7215	Intermediate Similarity	NPC475994
0.7215	Intermediate Similarity	NPC267231

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 NPC143396 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	2132
0.2-0.3	3913
0.3-0.4	2134
0.4-0.5	576
0.5-0.6	193
0.6-0.7	50
0.7-0.8	14
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4756	Discovery
0.8	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3197	Phase 1
0.7656	Intermediate Similarity	NPD3172	Approved
0.7654	Intermediate Similarity	NPD5363	Approved
0.7538	Intermediate Similarity	NPD4266	Approved
0.7538	Intermediate Similarity	NPD3195	Phase 2
0.7538	Intermediate Similarity	NPD3194	Approved
0.7538	Intermediate Similarity	NPD3196	Approved
0.7436	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4270	Approved
0.7284	Intermediate Similarity	NPD4269	Approved
0.725	Intermediate Similarity	NPD4252	Approved
0.7209	Intermediate Similarity	NPD5785	Approved
0.7077	Intermediate Similarity	NPD28	Approved
0.7077	Intermediate Similarity	NPD29	Approved
0.7031	Intermediate Similarity	NPD3173	Approved
0.7	Intermediate Similarity	NPD4268	Approved
0.7	Intermediate Similarity	NPD4271	Approved
0.6988	Remote Similarity	NPD5362	Discontinued
0.6988	Remote Similarity	NPD7154	Phase 3
0.6944	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5786	Approved
0.6875	Remote Similarity	NPD622	Approved
0.6829	Remote Similarity	NPD4822	Approved
0.6829	Remote Similarity	NPD5368	Approved
0.6829	Remote Similarity	NPD4820	Approved
0.6829	Remote Similarity	NPD4821	Approved
0.6829	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4819	Approved
0.6747	Remote Similarity	NPD5369	Approved
0.6742	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD3704	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6588	Remote Similarity	NPD5331	Approved
0.6588	Remote Similarity	NPD5332	Approved
0.6562	Remote Similarity	NPD3174	Discontinued
0.6562	Remote Similarity	NPD4222	Approved
0.6548	Remote Similarity	NPD4790	Discontinued
0.6517	Remote Similarity	NPD5370	Suspended
0.6515	Remote Similarity	NPD4220	Pre-registration
0.6452	Remote Similarity	NPD7839	Suspended
0.6447	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7331	Phase 2
0.6444	Remote Similarity	NPD6698	Approved
0.6444	Remote Similarity	NPD46	Approved
0.6444	Remote Similarity	NPD7838	Discovery
0.6429	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.642	Remote Similarity	NPD8039	Approved
0.6392	Remote Similarity	NPD6647	Phase 2
0.6374	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4249	Approved
0.6344	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6101	Approved
0.6333	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD39	Approved
0.6292	Remote Similarity	NPD4251	Approved
0.6292	Remote Similarity	NPD4250	Approved
0.6197	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7515	Phase 2
0.6196	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD3732	Approved
0.618	Remote Similarity	NPD5279	Phase 3
0.6164	Remote Similarity	NPD6109	Phase 1
0.6133	Remote Similarity	NPD4193	Approved
0.6133	Remote Similarity	NPD4192	Approved
0.6133	Remote Similarity	NPD4191	Approved
0.6133	Remote Similarity	NPD4194	Approved
0.6119	Remote Similarity	NPD5343	Approved
0.6104	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD1696	Phase 3
0.6067	Remote Similarity	NPD1694	Approved
0.6056	Remote Similarity	NPD3728	Approved
0.6056	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD3730	Approved
0.6022	Remote Similarity	NPD5281	Approved
0.6022	Remote Similarity	NPD5284	Approved
0.6022	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5326	Phase 3
0.5962	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD3666	Approved
0.5955	Remote Similarity	NPD3133	Approved
0.5955	Remote Similarity	NPD3665	Phase 1
0.5897	Remote Similarity	NPD7341	Phase 2
0.5895	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7748	Approved
0.5889	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6371	Approved
0.5862	Remote Similarity	NPD4695	Discontinued
0.5851	Remote Similarity	NPD6079	Approved
0.5843	Remote Similarity	NPD6110	Phase 1
0.5824	Remote Similarity	NPD3618	Phase 1
0.5824	Remote Similarity	NPD4519	Discontinued
0.5824	Remote Similarity	NPD4623	Approved
0.5821	Remote Similarity	NPD4265	Approved
0.5816	Remote Similarity	NPD4225	Approved
0.5806	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5211	Phase 2
0.5778	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5221	Approved
0.5773	Remote Similarity	NPD5222	Approved
0.5773	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD9411	Phase 1
0.5758	Remote Similarity	NPD7640	Approved
0.5758	Remote Similarity	NPD7639	Approved
0.573	Remote Similarity	NPD3667	Approved
0.5728	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD6084	Phase 2
0.5714	Remote Similarity	NPD5173	Approved
0.5714	Remote Similarity	NPD7902	Approved
0.5692	Remote Similarity	NPD2270	Approved
0.5688	Remote Similarity	NPD7115	Discovery
0.5686	Remote Similarity	NPD5141	Approved
0.5673	Remote Similarity	NPD6686	Approved
0.5673	Remote Similarity	NPD6881	Approved
0.5673	Remote Similarity	NPD6899	Approved
0.5673	Remote Similarity	NPD6011	Approved
0.5672	Remote Similarity	NPD6097	Approved
0.5672	Remote Similarity	NPD2699	Approved
0.5672	Remote Similarity	NPD6096	Approved
0.567	Remote Similarity	NPD4629	Approved
0.567	Remote Similarity	NPD5695	Phase 3
0.567	Remote Similarity	NPD5210	Approved
0.5657	Remote Similarity	NPD7638	Approved
0.5657	Remote Similarity	NPD9495	Approved
0.5652	Remote Similarity	NPD6409	Approved
0.5652	Remote Similarity	NPD7146	Approved
0.5652	Remote Similarity	NPD6684	Approved
0.5652	Remote Similarity	NPD5330	Approved
0.5652	Remote Similarity	NPD7521	Approved
0.5652	Remote Similarity	NPD6422	Discontinued
0.5652	Remote Similarity	NPD7334	Approved
0.5647	Remote Similarity	NPD8264	Approved
0.5641	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD5328	Approved
0.5638	Remote Similarity	NPD4753	Phase 2
0.5634	Remote Similarity	NPD6927	Phase 3
0.5631	Remote Similarity	NPD5048	Discontinued
0.5625	Remote Similarity	NPD6399	Phase 3
0.5625	Remote Similarity	NPD9655	Approved
0.5625	Remote Similarity	NPD9448	Phase 2
0.5625	Remote Similarity	NPD633	Phase 3
0.5619	Remote Similarity	NPD6014	Approved
0.5619	Remote Similarity	NPD6012	Approved
0.5619	Remote Similarity	NPD6013	Approved
0.5604	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD4786	Approved
0.56	Remote Similarity	NPD2066	Phase 3
0.56	Remote Similarity	NPD4696	Approved
0.56	Remote Similarity	NPD6404	Discontinued
0.56	Remote Similarity	NPD6648	Approved
0.56	Remote Similarity	NPD5285	Approved
0.56	Remote Similarity	NPD5286	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