NPASS Compound

Structure

NPC469747 OpenBabel07101718232D 31 32 0 0 1 0 0 0 0 0999 V2000 -2.0826 -15.7784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0881 -15.6739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6814 -14.7604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2691 -13.9514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8624 -13.0378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4502 -12.2288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0435 -11.3152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6312 -10.5062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2245 -9.5927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8123 -8.7837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4056 -7.8701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9933 -7.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5866 -6.1476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1744 -5.3385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7677 -4.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3554 -3.6160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 -1.8364 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 -1.7796 -1.0933 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 21 26 1 0 0 0 0 22 16 1 6 0 0 0 22 29 1 0 0 0 0 23 21 1 6 0 0 0 23 30 1 0 0 0 0 24 19 1 1 0 0 0 24 25 1 0 0 0 0 24 29 1 0 0 0 0 25 20 1 1 0 0 0 25 31 1 0 0 0 0 26 27 2 0 0 0 0 26 28 1 0 0 0 0 30 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.32
Volume:	477.181
LogP:	6.333
LogD:	4.124
LogS:	-4.248
# Rotatable Bonds:	16
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.162
Synthetic Accessibility Score:	4.21
Fsp3:	0.808
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:	-4.863
MDCK Permeability:	6.602274515898898e-05
Pgp-inhibitor:	0.599
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.207

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	97.7484359741211%
Volume Distribution (VD):	0.76
Pgp-substrate:	1.9655548334121704%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.16
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.992
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.368
CYP3A4-substrate:	0.074

ADMET: Excretion

Clearance (CL):	2.825
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.762
Human Hepatotoxicity (H-HT):	0.363
Drug-inuced Liver Injury (DILI):	0.626
AMES Toxicity:	0.839
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.977
Carcinogencity:	0.313
Eye Corrosion:	0.902
Eye Irritation:	0.87
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC469747

Natural Product ID:	NPC469747
*Common Name:**	Stolonic Acid A
IUPAC Name:	2-[(3S,6S)-6-[(2S,5R)-5-[(9E,11E)-hexadeca-9,11-dienyl]oxolan-2-yl]dioxan-3-yl]acetic acid
Synonyms:
Standard InCHIKey:	GAPWLWSFQQHPET-QMFURJOJSA-N
Standard InCHI:	InChI=1S/C26H44O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-22-17-19-24(29-22)25-20-18-23(30-31-25)21-26(27)28/h5-8,22-25H,2-4,9-21H2,1H3,(H,27,28)/b6-5+,8-7+/t22-,23+,24+,25+/m1/s1
SMILES:	CCCC/C=C/C=C/CCCCCCCC[C@@H]1CC[C@H](O1)[C@@H]1CC[C@H](OO1)CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1169554
PubChem CID:	49799949
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001312] 1,2-dioxanes

*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
NPO32632	stolonica sp.	Species	Styelidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[11076564]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[566422]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.05	ug.mL-1	PMID[566422]

☑ 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 NPC469747 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	135
0.1-0.2	1117
0.2-0.3	5663
0.3-0.4	14839
0.4-0.5	10668
0.5-0.6	8290
0.6-0.7	1871
0.7-0.8	109
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC263574
0.8889	High Similarity	NPC477994
0.8889	High Similarity	NPC477993
0.8375	Intermediate Similarity	NPC469920
0.8158	Intermediate Similarity	NPC476660
0.8049	Intermediate Similarity	NPC21693
0.8049	Intermediate Similarity	NPC236649
0.8026	Intermediate Similarity	NPC473772
0.8	Intermediate Similarity	NPC271921
0.8	Intermediate Similarity	NPC127091
0.8	Intermediate Similarity	NPC22101
0.8	Intermediate Similarity	NPC330426
0.8	Intermediate Similarity	NPC104537
0.8	Intermediate Similarity	NPC148192
0.7949	Intermediate Similarity	NPC326024
0.7922	Intermediate Similarity	NPC42526
0.7895	Intermediate Similarity	NPC141481
0.7895	Intermediate Similarity	NPC48218
0.7895	Intermediate Similarity	NPC473559
0.7895	Intermediate Similarity	NPC324981
0.7875	Intermediate Similarity	NPC190400
0.7875	Intermediate Similarity	NPC49392
0.7857	Intermediate Similarity	NPC470313
0.7857	Intermediate Similarity	NPC473500
0.7857	Intermediate Similarity	NPC38295
0.7857	Intermediate Similarity	NPC156089
0.7848	Intermediate Similarity	NPC474321
0.7821	Intermediate Similarity	NPC320119
0.7763	Intermediate Similarity	NPC475443
0.7763	Intermediate Similarity	NPC473829
0.7733	Intermediate Similarity	NPC318420
0.7733	Intermediate Similarity	NPC476654
0.7733	Intermediate Similarity	NPC476655
0.7733	Intermediate Similarity	NPC326268
0.7733	Intermediate Similarity	NPC476657
0.7703	Intermediate Similarity	NPC54925
0.7683	Intermediate Similarity	NPC218817
0.7683	Intermediate Similarity	NPC11796
0.7667	Intermediate Similarity	NPC478036
0.7667	Intermediate Similarity	NPC478037
0.7654	Intermediate Similarity	NPC239127
0.7654	Intermediate Similarity	NPC469514
0.7647	Intermediate Similarity	NPC69469
0.7632	Intermediate Similarity	NPC476656
0.7632	Intermediate Similarity	NPC476659
0.7564	Intermediate Similarity	NPC317583
0.7561	Intermediate Similarity	NPC110813
0.7561	Intermediate Similarity	NPC120776
0.7561	Intermediate Similarity	NPC240170
0.7561	Intermediate Similarity	NPC145898
0.7561	Intermediate Similarity	NPC281296
0.7531	Intermediate Similarity	NPC255060
0.75	Intermediate Similarity	NPC167145
0.75	Intermediate Similarity	NPC86005
0.7471	Intermediate Similarity	NPC471567
0.7471	Intermediate Similarity	NPC322529
0.7471	Intermediate Similarity	NPC120398
0.747	Intermediate Similarity	NPC133377
0.747	Intermediate Similarity	NPC121200
0.7444	Intermediate Similarity	NPC313670
0.7444	Intermediate Similarity	NPC473311
0.7416	Intermediate Similarity	NPC201046
0.7407	Intermediate Similarity	NPC330016
0.7386	Intermediate Similarity	NPC47937
0.7368	Intermediate Similarity	NPC469871
0.7368	Intermediate Similarity	NPC328089
0.7368	Intermediate Similarity	NPC68343
0.7368	Intermediate Similarity	NPC469870
0.7368	Intermediate Similarity	NPC476658
0.7356	Intermediate Similarity	NPC156804
0.7356	Intermediate Similarity	NPC163093
0.7347	Intermediate Similarity	NPC478038
0.7342	Intermediate Similarity	NPC470436
0.7333	Intermediate Similarity	NPC201939
0.7326	Intermediate Similarity	NPC474252
0.7303	Intermediate Similarity	NPC473995
0.7303	Intermediate Similarity	NPC477959
0.7284	Intermediate Similarity	NPC470435
0.7284	Intermediate Similarity	NPC325627
0.7273	Intermediate Similarity	NPC329615
0.7273	Intermediate Similarity	NPC136164
0.7273	Intermediate Similarity	NPC320642
0.7273	Intermediate Similarity	NPC329838
0.7273	Intermediate Similarity	NPC245947
0.7273	Intermediate Similarity	NPC477013
0.7273	Intermediate Similarity	NPC182383
0.7273	Intermediate Similarity	NPC477014
0.7273	Intermediate Similarity	NPC255863
0.7241	Intermediate Similarity	NPC253801
0.7229	Intermediate Similarity	NPC474447
0.7222	Intermediate Similarity	NPC89001
0.7222	Intermediate Similarity	NPC48338
0.7222	Intermediate Similarity	NPC233551
0.7222	Intermediate Similarity	NPC21208
0.7222	Intermediate Similarity	NPC280621
0.7222	Intermediate Similarity	NPC473905
0.7222	Intermediate Similarity	NPC20339
0.7222	Intermediate Similarity	NPC40376
0.7222	Intermediate Similarity	NPC320458
0.72	Intermediate Similarity	NPC81896
0.72	Intermediate Similarity	NPC328311
0.72	Intermediate Similarity	NPC243532
0.72	Intermediate Similarity	NPC321919
0.7195	Intermediate Similarity	NPC92558
0.7191	Intermediate Similarity	NPC171174
0.7191	Intermediate Similarity	NPC240695
0.7191	Intermediate Similarity	NPC475581
0.7191	Intermediate Similarity	NPC309211
0.7191	Intermediate Similarity	NPC142117
0.7191	Intermediate Similarity	NPC69082
0.7191	Intermediate Similarity	NPC279267
0.7191	Intermediate Similarity	NPC62118
0.7191	Intermediate Similarity	NPC114694
0.7191	Intermediate Similarity	NPC293136
0.7191	Intermediate Similarity	NPC232555
0.7191	Intermediate Similarity	NPC231096
0.7191	Intermediate Similarity	NPC477015
0.7191	Intermediate Similarity	NPC241360
0.7191	Intermediate Similarity	NPC107717
0.7191	Intermediate Similarity	NPC132940
0.7176	Intermediate Similarity	NPC308545
0.7176	Intermediate Similarity	NPC82488
0.7174	Intermediate Similarity	NPC327760
0.7158	Intermediate Similarity	NPC40812
0.7143	Intermediate Similarity	NPC256902
0.7143	Intermediate Similarity	NPC14901
0.7143	Intermediate Similarity	NPC477016
0.7143	Intermediate Similarity	NPC118193
0.7143	Intermediate Similarity	NPC130359
0.7143	Intermediate Similarity	NPC477017
0.7126	Intermediate Similarity	NPC65930
0.7126	Intermediate Similarity	NPC473780
0.7126	Intermediate Similarity	NPC180363
0.7126	Intermediate Similarity	NPC145914
0.7126	Intermediate Similarity	NPC473529
0.7126	Intermediate Similarity	NPC475159
0.7126	Intermediate Similarity	NPC11332
0.7126	Intermediate Similarity	NPC329829
0.7126	Intermediate Similarity	NPC73310
0.7126	Intermediate Similarity	NPC131002
0.7126	Intermediate Similarity	NPC94875
0.7126	Intermediate Similarity	NPC473712
0.7123	Intermediate Similarity	NPC18951
0.7111	Intermediate Similarity	NPC258068
0.7111	Intermediate Similarity	NPC178215
0.7111	Intermediate Similarity	NPC476583
0.7111	Intermediate Similarity	NPC20533
0.7108	Intermediate Similarity	NPC473948
0.7108	Intermediate Similarity	NPC217725
0.7108	Intermediate Similarity	NPC60718
0.7105	Intermediate Similarity	NPC321838
0.7105	Intermediate Similarity	NPC320305
0.7105	Intermediate Similarity	NPC328776
0.7093	Intermediate Similarity	NPC200446
0.7093	Intermediate Similarity	NPC472948
0.7089	Intermediate Similarity	NPC99619
0.7089	Intermediate Similarity	NPC26500
0.7083	Intermediate Similarity	NPC308567
0.7083	Intermediate Similarity	NPC261377
0.7083	Intermediate Similarity	NPC187761
0.7083	Intermediate Similarity	NPC255592
0.7083	Intermediate Similarity	NPC83895
0.7079	Intermediate Similarity	NPC473651
0.7079	Intermediate Similarity	NPC9678
0.7079	Intermediate Similarity	NPC25764
0.7079	Intermediate Similarity	NPC477018
0.7079	Intermediate Similarity	NPC103284
0.7079	Intermediate Similarity	NPC82795
0.7079	Intermediate Similarity	NPC39279
0.7079	Intermediate Similarity	NPC286338
0.7079	Intermediate Similarity	NPC223871
0.7079	Intermediate Similarity	NPC1083
0.7079	Intermediate Similarity	NPC110710
0.7079	Intermediate Similarity	NPC202055
0.7079	Intermediate Similarity	NPC475268
0.7079	Intermediate Similarity	NPC66346
0.7079	Intermediate Similarity	NPC470400
0.7079	Intermediate Similarity	NPC132496
0.7079	Intermediate Similarity	NPC283085
0.7079	Intermediate Similarity	NPC473671
0.7079	Intermediate Similarity	NPC107986
0.7079	Intermediate Similarity	NPC100921
0.7079	Intermediate Similarity	NPC319036
0.7079	Intermediate Similarity	NPC473478
0.7079	Intermediate Similarity	NPC473669
0.7079	Intermediate Similarity	NPC39167
0.7079	Intermediate Similarity	NPC235809
0.7079	Intermediate Similarity	NPC231009
0.7079	Intermediate Similarity	NPC473156
0.7079	Intermediate Similarity	NPC475206
0.7079	Intermediate Similarity	NPC77871
0.7079	Intermediate Similarity	NPC292809
0.7073	Intermediate Similarity	NPC329914
0.7071	Intermediate Similarity	NPC470519
0.7071	Intermediate Similarity	NPC469869
0.7071	Intermediate Similarity	NPC231271
0.7065	Intermediate Similarity	NPC239517
0.7065	Intermediate Similarity	NPC158388
0.7065	Intermediate Similarity	NPC478003
0.7065	Intermediate Similarity	NPC478004

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 NPC469747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	115
0.1-0.2	1680
0.2-0.3	4105
0.3-0.4	2222
0.4-0.5	649
0.5-0.6	334
0.6-0.7	44
0.7-0.8	1
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
0.7556	Intermediate Similarity	NPD7983	Approved
0.7143	Intermediate Similarity	NPD3197	Phase 1
0.7065	Intermediate Similarity	NPD6698	Approved
0.7065	Intermediate Similarity	NPD46	Approved
0.6957	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6101	Approved
0.6915	Remote Similarity	NPD5778	Approved
0.6915	Remote Similarity	NPD5779	Approved
0.6875	Remote Similarity	NPD7839	Suspended
0.6875	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3194	Approved
0.6849	Remote Similarity	NPD3195	Phase 2
0.6849	Remote Similarity	NPD4266	Approved
0.6849	Remote Similarity	NPD3196	Approved
0.6809	Remote Similarity	NPD6411	Approved
0.6753	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6435	Approved
0.6739	Remote Similarity	NPD4250	Approved
0.6739	Remote Similarity	NPD4251	Approved
0.6712	Remote Similarity	NPD3172	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.663	Remote Similarity	NPD4249	Approved
0.6629	Remote Similarity	NPD5369	Approved
0.6526	Remote Similarity	NPD7838	Discovery
0.6517	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5368	Approved
0.6494	Remote Similarity	NPD6109	Phase 1
0.6484	Remote Similarity	NPD7154	Phase 3
0.6458	Remote Similarity	NPD7637	Suspended
0.6442	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD28	Approved
0.6438	Remote Similarity	NPD29	Approved
0.6429	Remote Similarity	NPD8517	Approved
0.6429	Remote Similarity	NPD8515	Approved
0.6429	Remote Similarity	NPD8516	Approved
0.6429	Remote Similarity	NPD8513	Phase 3
0.64	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3728	Approved
0.64	Remote Similarity	NPD3730	Approved
0.6374	Remote Similarity	NPD4270	Approved
0.6374	Remote Similarity	NPD4269	Approved
0.6355	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4252	Approved
0.6292	Remote Similarity	NPD4271	Approved
0.6292	Remote Similarity	NPD4268	Approved
0.6277	Remote Similarity	NPD5786	Approved
0.6226	Remote Similarity	NPD6686	Approved
0.618	Remote Similarity	NPD4756	Discovery
0.617	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5363	Approved
0.6164	Remote Similarity	NPD3173	Approved
0.6154	Remote Similarity	NPD4820	Approved
0.6154	Remote Similarity	NPD8074	Phase 3
0.6154	Remote Similarity	NPD4819	Approved
0.6154	Remote Similarity	NPD4822	Approved
0.6154	Remote Similarity	NPD4821	Approved
0.614	Remote Similarity	NPD8444	Approved
0.6136	Remote Similarity	NPD8039	Approved
0.6129	Remote Similarity	NPD5362	Discontinued
0.6111	Remote Similarity	NPD3732	Approved
0.6111	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6371	Approved
0.61	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7829	Approved
0.6034	Remote Similarity	NPD7830	Approved
0.6027	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD622	Approved
0.6027	Remote Similarity	NPD5343	Approved
0.602	Remote Similarity	NPD5785	Approved
0.6018	Remote Similarity	NPD7641	Discontinued
0.5983	Remote Similarity	NPD8341	Approved
0.5983	Remote Similarity	NPD8299	Approved
0.5983	Remote Similarity	NPD8340	Approved
0.5983	Remote Similarity	NPD8342	Approved
0.5981	Remote Similarity	NPD6412	Phase 2
0.596	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6422	Discontinued
0.5932	Remote Similarity	NPD8451	Approved
0.5932	Remote Similarity	NPD8273	Phase 1
0.5926	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5370	Suspended
0.59	Remote Similarity	NPD6399	Phase 3
0.5882	Remote Similarity	NPD8448	Approved
0.5865	Remote Similarity	NPD6648	Approved
0.5851	Remote Similarity	NPD5209	Approved
0.5847	Remote Similarity	NPD7492	Approved
0.5833	Remote Similarity	NPD6685	Approved
0.5818	Remote Similarity	NPD6421	Discontinued
0.5798	Remote Similarity	NPD6616	Approved
0.5789	Remote Similarity	NPD6935	Phase 3
0.5789	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6054	Approved
0.5776	Remote Similarity	NPD6319	Approved
0.5769	Remote Similarity	NPD4225	Approved
0.5758	Remote Similarity	NPD1695	Approved
0.5753	Remote Similarity	NPD4222	Approved
0.5753	Remote Similarity	NPD3174	Discontinued
0.5753	Remote Similarity	NPD39	Approved
0.575	Remote Similarity	NPD7078	Approved
0.575	Remote Similarity	NPD8959	Approved
0.5741	Remote Similarity	NPD5048	Discontinued
0.5738	Remote Similarity	NPD8390	Approved
0.5738	Remote Similarity	NPD8391	Approved
0.5738	Remote Similarity	NPD8392	Approved
0.5714	Remote Similarity	NPD818	Approved
0.5714	Remote Similarity	NPD819	Approved
0.5714	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7736	Approved
0.57	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD897	Approved
0.5698	Remote Similarity	NPD898	Approved
0.5698	Remote Similarity	NPD896	Approved
0.5678	Remote Similarity	NPD6370	Approved
0.567	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5344	Discontinued
0.5652	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD7500	Approved
0.5641	Remote Similarity	NPD6059	Approved
0.563	Remote Similarity	NPD8328	Phase 3
0.563	Remote Similarity	NPD7642	Approved
0.5625	Remote Similarity	NPD5331	Approved
0.5625	Remote Similarity	NPD5332	Approved
0.562	Remote Similarity	NPD8293	Discontinued
0.5619	Remote Similarity	NPD7638	Approved
0.5616	Remote Similarity	NPD6097	Approved
0.5616	Remote Similarity	NPD2699	Approved
0.5616	Remote Similarity	NPD6096	Approved
0.5603	Remote Similarity	NPD6918	Phase 1

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