NPASS Compound

Structure

CID100487 OpenBabel06191715442D 27 29 0 0 1 0 0 0 0 0999 V2000 -3.2453 -4.8652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8566 -6.0028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4586 1.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3272 -2.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4546 -2.4237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5330 -5.5670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0341 0.5138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5690 -5.3010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0342 0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5410 -2.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3288 -0.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5111 -1.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7971 -2.4703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7782 -2.6635 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3174 -4.3332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7110 -0.4175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2752 -0.7650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1972 -3.2704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3534 -4.0671 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8574 -0.9385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0298 -3.6314 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 6 1 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 19 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 21 2 0 0 0 0 13 10 1 6 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 1 0 0 0 16 26 1 6 0 0 0 17 20 1 1 0 0 0 17 27 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.14
Volume:	371.883
LogP:	1.051
LogD:	0.825
LogS:	-2.769
# Rotatable Bonds:	3
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	5.067
Fsp3:	0.45
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:	-4.84
MDCK Permeability:	2.0443330868147314e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.122
Human Intestinal Absorption (HIA):	0.058
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.328
Plasma Protein Binding (PPB):	69.49449920654297%
Volume Distribution (VD):	0.528
Pgp-substrate:	28.95084571838379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.096
CYP2C19-substrate:	0.439
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.104
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	3.697
Half-life (T1/2):	0.449

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.358
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.899
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.938
Carcinogencity:	0.151
Eye Corrosion:	0.664
Eye Irritation:	0.553
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: NPC100487

Natural Product ID:	NPC100487
*Common Name:**	Pumilin
IUPAC Name:	[(3aR,4R,5R,9aR,9bS)-4,9a-dihydroxy-6,9-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,9b-tetrahydroazuleno[4,5-b]furan-5-yl] (Z)-2-methylbut-2-enoate
Synonyms:	Pumilin
Standard InCHIKey:	SLZLXIXUYNEOBA-MELKTAGESA-N
Standard InCHI:	InChI=1S/C20H22O7/c1-6-8(2)18(23)26-16-11(5)14-12(21)7-9(3)20(14,25)17-13(15(16)22)10(4)19(24)27-17/h6-7,13,15-17,22,25H,4H2,1-3,5H3/b8-6-/t13-,15-,16-,17+,20-/m1/s1
SMILES:	C/C=C(/C)C(=O)O[C@@H]1C(=C2C(=O)C=C(C)[C@@]2([C@@H]2[C@H](C(=C)C(=O)O2)[C@H]1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517308
PubChem CID:	6436294
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO11087	Berlandiera pumila	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11087	Berlandiera pumila	Species	Asteraceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	128.0	ug.mL-1	PMID[456109]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	MIC	=	128.0	ug.mL-1	PMID[456109]

☑ 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 NPC100487 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	233
0.1-0.2	1291
0.2-0.3	4539
0.3-0.4	7921
0.4-0.5	14551
0.5-0.6	8129
0.6-0.7	4170
0.7-0.8	1525
0.8-0.85	257
0.85-0.9	77
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9109	High Similarity	NPC243998
0.901	High Similarity	NPC203659
0.8958	High Similarity	NPC475912
0.8922	High Similarity	NPC223450
0.8911	High Similarity	NPC475871
0.8911	High Similarity	NPC110989
0.8911	High Similarity	NPC475945
0.89	High Similarity	NPC150923
0.8812	High Similarity	NPC474747
0.8812	High Similarity	NPC225353
0.8812	High Similarity	NPC86077
0.88	High Similarity	NPC288876
0.8776	High Similarity	NPC270013
0.8776	High Similarity	NPC36954
0.8776	High Similarity	NPC14961
0.8763	High Similarity	NPC81419
0.8763	High Similarity	NPC179746
0.875	High Similarity	NPC71533
0.875	High Similarity	NPC129419
0.875	High Similarity	NPC106510
0.8713	High Similarity	NPC185141
0.8713	High Similarity	NPC110443
0.8713	High Similarity	NPC133907
0.8713	High Similarity	NPC474742
0.8713	High Similarity	NPC128733
0.8713	High Similarity	NPC46998
0.8673	High Similarity	NPC81386
0.8673	High Similarity	NPC474035
0.866	High Similarity	NPC208886
0.866	High Similarity	NPC12172
0.866	High Similarity	NPC184463
0.866	High Similarity	NPC30515
0.8654	High Similarity	NPC26617
0.8646	High Similarity	NPC268298
0.8641	High Similarity	NPC474741
0.8627	High Similarity	NPC149371
0.8598	High Similarity	NPC258711
0.8598	High Similarity	NPC35069
0.8586	High Similarity	NPC304886
0.8586	High Similarity	NPC471142
0.8585	High Similarity	NPC257240
0.8571	High Similarity	NPC162205
0.8571	High Similarity	NPC295204
0.8571	High Similarity	NPC212486
0.8571	High Similarity	NPC273579
0.8571	High Similarity	NPC135776
0.8571	High Similarity	NPC288240
0.8571	High Similarity	NPC476300
0.8557	High Similarity	NPC476004
0.8557	High Similarity	NPC51004
0.8557	High Similarity	NPC474761
0.8544	High Similarity	NPC472755
0.8542	High Similarity	NPC202672
0.8529	High Similarity	NPC47880
0.8529	High Similarity	NPC171759
0.8515	High Similarity	NPC473326
0.8515	High Similarity	NPC141191
0.8515	High Similarity	NPC187268
0.8515	High Similarity	NPC471144
0.85	High Similarity	NPC473859
0.85	High Similarity	NPC477921
0.85	High Similarity	NPC476315
0.8491	Intermediate Similarity	NPC38154
0.8485	Intermediate Similarity	NPC477131
0.8469	Intermediate Similarity	NPC473321
0.8469	Intermediate Similarity	NPC300312
0.8469	Intermediate Similarity	NPC261607
0.8469	Intermediate Similarity	NPC111114
0.8454	Intermediate Similarity	NPC307411
0.8454	Intermediate Similarity	NPC295312
0.8431	Intermediate Similarity	NPC70865
0.8426	Intermediate Similarity	NPC189338
0.8426	Intermediate Similarity	NPC95290
0.8416	Intermediate Similarity	NPC108475
0.8416	Intermediate Similarity	NPC169205
0.8416	Intermediate Similarity	NPC161493
0.8416	Intermediate Similarity	NPC170143
0.8416	Intermediate Similarity	NPC40812
0.8416	Intermediate Similarity	NPC213947
0.8411	Intermediate Similarity	NPC477103
0.84	Intermediate Similarity	NPC52044
0.84	Intermediate Similarity	NPC475659
0.84	Intermediate Similarity	NPC477922
0.84	Intermediate Similarity	NPC213698
0.84	Intermediate Similarity	NPC67584
0.84	Intermediate Similarity	NPC170120
0.8384	Intermediate Similarity	NPC469645
0.8384	Intermediate Similarity	NPC469692
0.8381	Intermediate Similarity	NPC54737
0.8378	Intermediate Similarity	NPC475309
0.8367	Intermediate Similarity	NPC473619
0.8367	Intermediate Similarity	NPC77337
0.8365	Intermediate Similarity	NPC124881
0.8365	Intermediate Similarity	NPC475873
0.8351	Intermediate Similarity	NPC153805
0.835	Intermediate Similarity	NPC201718
0.835	Intermediate Similarity	NPC472753
0.835	Intermediate Similarity	NPC476270
0.835	Intermediate Similarity	NPC474339
0.835	Intermediate Similarity	NPC164598
0.8349	Intermediate Similarity	NPC106395
0.8349	Intermediate Similarity	NPC46269
0.8333	Intermediate Similarity	NPC287311
0.8333	Intermediate Similarity	NPC83895
0.8333	Intermediate Similarity	NPC474213
0.8333	Intermediate Similarity	NPC187761
0.8318	Intermediate Similarity	NPC477102
0.8317	Intermediate Similarity	NPC213078
0.8317	Intermediate Similarity	NPC476009
0.8317	Intermediate Similarity	NPC230800
0.8317	Intermediate Similarity	NPC279621
0.8317	Intermediate Similarity	NPC185553
0.8302	Intermediate Similarity	NPC477513
0.83	Intermediate Similarity	NPC121825
0.83	Intermediate Similarity	NPC303942
0.83	Intermediate Similarity	NPC127019
0.83	Intermediate Similarity	NPC323008
0.83	Intermediate Similarity	NPC262133
0.83	Intermediate Similarity	NPC470010
0.83	Intermediate Similarity	NPC57405
0.83	Intermediate Similarity	NPC198853
0.83	Intermediate Similarity	NPC470013
0.8288	Intermediate Similarity	NPC471145
0.8283	Intermediate Similarity	NPC131209
0.8283	Intermediate Similarity	NPC133698
0.8273	Intermediate Similarity	NPC138303
0.8273	Intermediate Similarity	NPC67290
0.8273	Intermediate Similarity	NPC133677
0.8269	Intermediate Similarity	NPC472754
0.8265	Intermediate Similarity	NPC32922
0.8265	Intermediate Similarity	NPC474032
0.8257	Intermediate Similarity	NPC138757
0.8257	Intermediate Similarity	NPC76550
0.8257	Intermediate Similarity	NPC123855
0.8247	Intermediate Similarity	NPC186148
0.8247	Intermediate Similarity	NPC237540
0.8235	Intermediate Similarity	NPC471150
0.8235	Intermediate Similarity	NPC474313
0.8229	Intermediate Similarity	NPC21469
0.8229	Intermediate Similarity	NPC165162
0.8224	Intermediate Similarity	NPC117604
0.8224	Intermediate Similarity	NPC475960
0.8224	Intermediate Similarity	NPC308191
0.8218	Intermediate Similarity	NPC48803
0.8218	Intermediate Similarity	NPC90121
0.8218	Intermediate Similarity	NPC193645
0.8218	Intermediate Similarity	NPC475900
0.8218	Intermediate Similarity	NPC275960
0.8208	Intermediate Similarity	NPC179891
0.82	Intermediate Similarity	NPC125674
0.82	Intermediate Similarity	NPC228451
0.82	Intermediate Similarity	NPC475838
0.8182	Intermediate Similarity	NPC179394
0.8182	Intermediate Similarity	NPC475855
0.8182	Intermediate Similarity	NPC144133
0.8163	Intermediate Similarity	NPC474471
0.8163	Intermediate Similarity	NPC58219
0.8163	Intermediate Similarity	NPC473715
0.8163	Intermediate Similarity	NPC227379
0.8163	Intermediate Similarity	NPC177629
0.8155	Intermediate Similarity	NPC308567
0.8155	Intermediate Similarity	NPC261377
0.8155	Intermediate Similarity	NPC255592
0.8155	Intermediate Similarity	NPC221615
0.8148	Intermediate Similarity	NPC59489
0.8148	Intermediate Similarity	NPC139838
0.8144	Intermediate Similarity	NPC107787
0.8137	Intermediate Similarity	NPC39859
0.8137	Intermediate Similarity	NPC470883
0.8137	Intermediate Similarity	NPC91771
0.8137	Intermediate Similarity	NPC142529
0.8137	Intermediate Similarity	NPC126156
0.8137	Intermediate Similarity	NPC76862
0.8137	Intermediate Similarity	NPC158416
0.8125	Intermediate Similarity	NPC471146
0.8125	Intermediate Similarity	NPC115786
0.8119	Intermediate Similarity	NPC473316
0.8119	Intermediate Similarity	NPC473330
0.8119	Intermediate Similarity	NPC474247
0.8119	Intermediate Similarity	NPC167219
0.8119	Intermediate Similarity	NPC469632
0.8119	Intermediate Similarity	NPC474338
0.8119	Intermediate Similarity	NPC140543
0.8113	Intermediate Similarity	NPC309190
0.8113	Intermediate Similarity	NPC472756
0.81	Intermediate Similarity	NPC475925
0.81	Intermediate Similarity	NPC476705
0.81	Intermediate Similarity	NPC184063
0.8095	Intermediate Similarity	NPC320019
0.8095	Intermediate Similarity	NPC471148
0.8095	Intermediate Similarity	NPC324017
0.8081	Intermediate Similarity	NPC92974
0.8077	Intermediate Similarity	NPC475949
0.8077	Intermediate Similarity	NPC280963
0.8061	Intermediate Similarity	NPC160138
0.8061	Intermediate Similarity	NPC248602
0.8061	Intermediate Similarity	NPC231889
0.8058	Intermediate Similarity	NPC311904
0.8058	Intermediate Similarity	NPC471462
0.8041	Intermediate Similarity	NPC137033

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 NPC100487 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1913
0.2-0.3	3629
0.3-0.4	2184
0.4-0.5	792
0.5-0.6	289
0.6-0.7	110
0.7-0.8	15
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD7899	Clinical (unspecified phase)
0.8585	High Similarity	NPD6371	Approved
0.8218	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD7983	Approved
0.7647	Intermediate Similarity	NPD46	Approved
0.7647	Intermediate Similarity	NPD6698	Approved
0.7549	Intermediate Similarity	NPD1695	Approved
0.75	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD5785	Approved
0.7327	Intermediate Similarity	NPD5363	Approved
0.7315	Intermediate Similarity	NPD4225	Approved
0.7308	Intermediate Similarity	NPD7838	Discovery
0.7304	Intermediate Similarity	NPD6053	Discontinued
0.7264	Intermediate Similarity	NPD5282	Discontinued
0.7255	Intermediate Similarity	NPD5786	Approved
0.7087	Intermediate Similarity	NPD4249	Approved
0.7069	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7115	Discovery
0.703	Intermediate Similarity	NPD4269	Approved
0.703	Intermediate Similarity	NPD4270	Approved
0.7019	Intermediate Similarity	NPD4251	Approved
0.7019	Intermediate Similarity	NPD4250	Approved
0.7009	Intermediate Similarity	NPD5779	Approved
0.7009	Intermediate Similarity	NPD5778	Approved
0.7	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD8513	Phase 3
0.6967	Remote Similarity	NPD8517	Approved
0.6967	Remote Similarity	NPD8516	Approved
0.6967	Remote Similarity	NPD8515	Approved
0.6961	Remote Similarity	NPD5362	Discontinued
0.6961	Remote Similarity	NPD7154	Phase 3
0.6957	Remote Similarity	NPD6686	Approved
0.6931	Remote Similarity	NPD5369	Approved
0.6885	Remote Similarity	NPD6319	Approved
0.6875	Remote Similarity	NPD5344	Discontinued
0.6863	Remote Similarity	NPD6435	Approved
0.685	Remote Similarity	NPD7319	Approved
0.6832	Remote Similarity	NPD4252	Approved
0.68	Remote Similarity	NPD7492	Approved
0.6748	Remote Similarity	NPD6054	Approved
0.6746	Remote Similarity	NPD6616	Approved
0.6746	Remote Similarity	NPD7507	Approved
0.672	Remote Similarity	NPD7642	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6693	Remote Similarity	NPD7078	Approved
0.6693	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6641	Remote Similarity	NPD7736	Approved
0.664	Remote Similarity	NPD6370	Approved
0.664	Remote Similarity	NPD5988	Approved
0.6638	Remote Similarity	NPD6008	Approved
0.6613	Remote Similarity	NPD6059	Approved
0.6562	Remote Similarity	NPD8293	Discontinued
0.6538	Remote Similarity	NPD5209	Approved
0.6525	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6648	Approved
0.6491	Remote Similarity	NPD7639	Approved
0.6491	Remote Similarity	NPD7640	Approved
0.6471	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4271	Approved
0.6471	Remote Similarity	NPD4268	Approved
0.6457	Remote Similarity	NPD7829	Approved
0.6457	Remote Similarity	NPD7830	Approved
0.6446	Remote Similarity	NPD8297	Approved
0.6441	Remote Similarity	NPD5697	Approved
0.6441	Remote Similarity	NPD6412	Phase 2
0.6422	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6101	Approved
0.6417	Remote Similarity	NPD4634	Approved
0.6404	Remote Similarity	NPD7638	Approved
0.6387	Remote Similarity	NPD7320	Approved
0.6387	Remote Similarity	NPD6899	Approved
0.6387	Remote Similarity	NPD6881	Approved
0.6381	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6009	Approved
0.6364	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD6649	Approved
0.6357	Remote Similarity	NPD8451	Approved
0.6357	Remote Similarity	NPD8273	Phase 1
0.6356	Remote Similarity	NPD7128	Approved
0.6356	Remote Similarity	NPD6675	Approved
0.6356	Remote Similarity	NPD6402	Approved
0.6356	Remote Similarity	NPD5739	Approved
0.6355	Remote Similarity	NPD1694	Approved
0.6333	Remote Similarity	NPD6012	Approved
0.6333	Remote Similarity	NPD6373	Approved
0.6333	Remote Similarity	NPD6014	Approved
0.6333	Remote Similarity	NPD6013	Approved
0.6333	Remote Similarity	NPD6372	Approved
0.6321	Remote Similarity	NPD5332	Approved
0.6321	Remote Similarity	NPD5331	Approved
0.6321	Remote Similarity	NPD6110	Phase 1
0.632	Remote Similarity	NPD7641	Discontinued
0.6311	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8448	Approved
0.6306	Remote Similarity	NPD6411	Approved
0.6306	Remote Similarity	NPD7637	Suspended
0.6303	Remote Similarity	NPD5701	Approved
0.6299	Remote Similarity	NPD8444	Approved
0.6299	Remote Similarity	NPD5983	Phase 2
0.6286	Remote Similarity	NPD4790	Discontinued
0.6281	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6883	Approved
0.6281	Remote Similarity	NPD7290	Approved
0.6281	Remote Similarity	NPD7102	Approved
0.6279	Remote Similarity	NPD8340	Approved
0.6279	Remote Similarity	NPD8342	Approved
0.6279	Remote Similarity	NPD8341	Approved
0.6279	Remote Similarity	NPD8299	Approved
0.6273	Remote Similarity	NPD5370	Suspended
0.625	Remote Similarity	NPD6011	Approved
0.6241	Remote Similarity	NPD7260	Phase 2
0.6239	Remote Similarity	NPD5211	Phase 2
0.623	Remote Similarity	NPD2204	Approved
0.623	Remote Similarity	NPD8130	Phase 1
0.623	Remote Similarity	NPD6847	Approved
0.623	Remote Similarity	NPD6617	Approved
0.623	Remote Similarity	NPD6869	Approved
0.6226	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD7604	Phase 2
0.6202	Remote Similarity	NPD8328	Phase 3
0.6194	Remote Similarity	NPD6845	Suspended
0.619	Remote Similarity	NPD7328	Approved
0.619	Remote Similarity	NPD7327	Approved
0.6179	Remote Similarity	NPD6882	Approved
0.6174	Remote Similarity	NPD6084	Phase 2
0.6174	Remote Similarity	NPD6083	Phase 2
0.6172	Remote Similarity	NPD8266	Approved
0.6172	Remote Similarity	NPD8267	Approved
0.6172	Remote Similarity	NPD8268	Approved
0.6172	Remote Similarity	NPD8269	Approved
0.6172	Remote Similarity	NPD8033	Approved
0.6165	Remote Similarity	NPD8392	Approved
0.6165	Remote Similarity	NPD8391	Approved
0.6165	Remote Similarity	NPD8390	Approved
0.6161	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7516	Approved
0.614	Remote Similarity	NPD5695	Phase 3
0.6136	Remote Similarity	NPD6033	Approved
0.6134	Remote Similarity	NPD5141	Approved
0.6124	Remote Similarity	NPD8080	Discontinued
0.6121	Remote Similarity	NPD5696	Approved
0.6111	Remote Similarity	NPD7500	Approved
0.6107	Remote Similarity	NPD6336	Discontinued
0.6106	Remote Similarity	NPD6399	Phase 3
0.6094	Remote Similarity	NPD8294	Approved
0.6094	Remote Similarity	NPD8377	Approved
0.6068	Remote Similarity	NPD5286	Approved
0.6068	Remote Similarity	NPD4696	Approved
0.6068	Remote Similarity	NPD5285	Approved
0.6047	Remote Similarity	NPD8335	Approved
0.6047	Remote Similarity	NPD8378	Approved
0.6047	Remote Similarity	NPD8296	Approved
0.6047	Remote Similarity	NPD8380	Approved
0.6047	Remote Similarity	NPD8379	Approved
0.6047	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7503	Approved
0.6045	Remote Similarity	NPD5956	Approved
0.6034	Remote Similarity	NPD4755	Approved
0.6033	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6274	Approved
0.5984	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD5225	Approved
0.5966	Remote Similarity	NPD4633	Approved
0.5966	Remote Similarity	NPD7632	Discontinued
0.5966	Remote Similarity	NPD5226	Approved
0.5966	Remote Similarity	NPD5224	Approved
0.5963	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7524	Approved
0.5942	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4700	Approved
0.5923	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD6921	Approved
0.5918	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD5174	Approved
0.5917	Remote Similarity	NPD5175	Approved
0.5905	Remote Similarity	NPD4756	Discovery
0.5893	Remote Similarity	NPD6903	Approved
0.5891	Remote Similarity	NPD7101	Approved
0.5891	Remote Similarity	NPD7100	Approved
0.5887	Remote Similarity	NPD6421	Discontinued
0.5882	Remote Similarity	NPD5223	Approved
0.5877	Remote Similarity	NPD5281	Approved
0.5877	Remote Similarity	NPD5284	Approved
0.5877	Remote Similarity	NPD5693	Phase 1
0.5868	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5210	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