NPASS Compound

Structure

CID50223 OpenBabel06191715382D 27 30 0 0 1 0 0 0 0 0999 V2000 -2.9638 -1.1676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2049 3.1079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2025 2.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1063 1.7423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3180 -1.1737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3180 0.7388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4899 1.2169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0357 -0.4768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1462 -0.6956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0950 2.7585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5315 2.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1462 0.2607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4899 -0.6956 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6049 -0.2173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1899 0.6442 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1901 -1.0790 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2576 0.8569 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4899 0.2607 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3951 -0.2693 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8425 3.3547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6060 2.5541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9638 0.7327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5147 -0.2172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2375 1.8130 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 1.7860 1.3919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2578 -1.2917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 17 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 6 18 1 0 0 0 0 7 24 1 0 0 0 0 8 19 1 0 0 0 0 8 25 1 0 0 0 0 9 12 1 0 0 0 0 10 20 2 0 0 0 0 10 24 1 0 0 0 0 11 21 2 0 0 0 0 11 26 1 0 0 0 0 12 22 2 0 0 0 0 13 18 1 6 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 1 0 0 0 15 17 1 6 0 0 0 15 26 1 0 0 0 0 16 19 1 6 0 0 0 16 27 1 0 0 0 0 17 18 1 1 0 0 0 18 7 1 1 0 0 0 19 17 1 1 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.15
Volume:	362.73
LogP:	0.836
LogD:	0.725
LogS:	-3.83
# Rotatable Bonds:	5
TPSA:	111.66
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	5.972
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.256
MDCK Permeability:	4.6851186198182404e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.276
Human Intestinal Absorption (HIA):	0.068
20% Bioavailability (F20%):	0.64
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.785
Plasma Protein Binding (PPB):	26.912704467773438%
Volume Distribution (VD):	0.524
Pgp-substrate:	66.21404266357422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.62
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.295
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	2.509
Half-life (T1/2):	0.784

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.555
AMES Toxicity:	0.473
Rat Oral Acute Toxicity:	0.29
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.844
Carcinogencity:	0.795
Eye Corrosion:	0.005
Eye Irritation:	0.059
Respiratory Toxicity:	0.409

Download Data

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

Natural Product: NPC50223

Natural Product ID:	NPC50223
*Common Name:**	FAQMCKSIBZGZIB-NMAPUUFXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FAQMCKSIBZGZIB-NMAPUUFXSA-N
Standard InCHI:	InChI=1S/C19H24O8/c1-9-5-13-18(6-12(9)22,7-24-10(2)20)17(4)15(26-11(3)21)14(23)16(27-13)19(17)8-25-19/h5,13-16,23H,6-8H2,1-4H3/t13-,14-,15-,16-,17-,18-,19+/m1/s1
SMILES:	CC(=O)OC[C@]12CC(=O)C(=C[C@H]1O[C@H]1[C@]3([C@]2(C)[C@H](OC(=O)C)[C@H]1O)CO3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL149588
PubChem CID:	156895
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800633]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8289061]
NPO10844	Lactarius pergamenus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4524	Bosistoa pentacocca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10844	Lactarius pergamenus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	LC50	=	0.0069	ug.mL-1	PMID[525702]

☑ 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 NPC50223 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	214
0.1-0.2	1286
0.2-0.3	4661
0.3-0.4	8282
0.4-0.5	13307
0.5-0.6	7366
0.6-0.7	5645
0.7-0.8	1782
0.8-0.85	101
0.85-0.9	41
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC41551
0.9406	High Similarity	NPC123505
0.9314	High Similarity	NPC169843
0.9143	High Similarity	NPC77089
0.9029	High Similarity	NPC474783
0.9029	High Similarity	NPC260809
0.8932	High Similarity	NPC252242
0.8932	High Similarity	NPC475956
0.8922	High Similarity	NPC79631
0.8899	High Similarity	NPC305044
0.8899	High Similarity	NPC265290
0.8889	High Similarity	NPC313921
0.8889	High Similarity	NPC98038
0.8835	High Similarity	NPC26557
0.8824	High Similarity	NPC474957
0.8824	High Similarity	NPC79449
0.8807	High Similarity	NPC101400
0.8807	High Similarity	NPC101965
0.8796	High Similarity	NPC474750
0.875	High Similarity	NPC214714
0.875	High Similarity	NPC475986
0.875	High Similarity	NPC200672
0.8725	High Similarity	NPC476057
0.8725	High Similarity	NPC347923
0.8713	High Similarity	NPC240838
0.8679	High Similarity	NPC469960
0.8679	High Similarity	NPC29389
0.8679	High Similarity	NPC93026
0.8679	High Similarity	NPC265502
0.8667	High Similarity	NPC232515
0.8661	High Similarity	NPC474286
0.8661	High Similarity	NPC475130
0.8641	High Similarity	NPC274458
0.8611	High Similarity	NPC187876
0.8598	High Similarity	NPC472263
0.8598	High Similarity	NPC469957
0.8598	High Similarity	NPC108682
0.8598	High Similarity	NPC469959
0.8544	High Similarity	NPC182811
0.8519	High Similarity	NPC10150
0.8496	Intermediate Similarity	NPC475401
0.8421	Intermediate Similarity	NPC477092
0.8407	Intermediate Similarity	NPC475305
0.8348	Intermediate Similarity	NPC79579
0.8333	Intermediate Similarity	NPC54737
0.8273	Intermediate Similarity	NPC59489
0.8273	Intermediate Similarity	NPC139838
0.8261	Intermediate Similarity	NPC5292
0.8214	Intermediate Similarity	NPC126691
0.8208	Intermediate Similarity	NPC13743
0.8208	Intermediate Similarity	NPC98813
0.8174	Intermediate Similarity	NPC153440
0.8142	Intermediate Similarity	NPC287075
0.8125	Intermediate Similarity	NPC475495
0.812	Intermediate Similarity	NPC472001
0.812	Intermediate Similarity	NPC310511
0.812	Intermediate Similarity	NPC472000
0.812	Intermediate Similarity	NPC471999
0.8113	Intermediate Similarity	NPC222303
0.8113	Intermediate Similarity	NPC65700
0.807	Intermediate Similarity	NPC178289
0.8053	Intermediate Similarity	NPC475277
0.8053	Intermediate Similarity	NPC477093
0.8053	Intermediate Similarity	NPC473522
0.8051	Intermediate Similarity	NPC107493
0.8037	Intermediate Similarity	NPC280963
0.8036	Intermediate Similarity	NPC5103
0.8036	Intermediate Similarity	NPC193741
0.8034	Intermediate Similarity	NPC474585
0.8018	Intermediate Similarity	NPC472825
0.8	Intermediate Similarity	NPC190286
0.8	Intermediate Similarity	NPC270013
0.8	Intermediate Similarity	NPC14961
0.8	Intermediate Similarity	NPC223450
0.8	Intermediate Similarity	NPC243998
0.7983	Intermediate Similarity	NPC469789
0.7982	Intermediate Similarity	NPC474775
0.7982	Intermediate Similarity	NPC962
0.7982	Intermediate Similarity	NPC317210
0.7982	Intermediate Similarity	NPC250109
0.7981	Intermediate Similarity	NPC212486
0.7966	Intermediate Similarity	NPC46570
0.7963	Intermediate Similarity	NPC150923
0.7961	Intermediate Similarity	NPC197107
0.7951	Intermediate Similarity	NPC470880
0.7949	Intermediate Similarity	NPC475041
0.7949	Intermediate Similarity	NPC305260
0.7949	Intermediate Similarity	NPC472667
0.7949	Intermediate Similarity	NPC473203
0.7949	Intermediate Similarity	NPC270850
0.7944	Intermediate Similarity	NPC212465
0.7944	Intermediate Similarity	NPC177232
0.7934	Intermediate Similarity	NPC287423
0.7928	Intermediate Similarity	NPC470192
0.7925	Intermediate Similarity	NPC476315
0.7917	Intermediate Similarity	NPC172154
0.7917	Intermediate Similarity	NPC81736
0.7909	Intermediate Similarity	NPC470104
0.7905	Intermediate Similarity	NPC474035
0.7905	Intermediate Similarity	NPC81386
0.7899	Intermediate Similarity	NPC23786
0.7899	Intermediate Similarity	NPC269642
0.7899	Intermediate Similarity	NPC470265
0.7895	Intermediate Similarity	NPC475924
0.7895	Intermediate Similarity	NPC475851
0.7895	Intermediate Similarity	NPC317687
0.7895	Intermediate Similarity	NPC236217
0.7886	Intermediate Similarity	NPC213634
0.7881	Intermediate Similarity	NPC143755
0.7881	Intermediate Similarity	NPC472004
0.7876	Intermediate Similarity	NPC206595
0.7876	Intermediate Similarity	NPC477103
0.787	Intermediate Similarity	NPC186861
0.787	Intermediate Similarity	NPC471381
0.7863	Intermediate Similarity	NPC13710
0.7851	Intermediate Similarity	NPC293112
0.7851	Intermediate Similarity	NPC473635
0.785	Intermediate Similarity	NPC471150
0.785	Intermediate Similarity	NPC40812
0.7845	Intermediate Similarity	NPC298278
0.7845	Intermediate Similarity	NPC106228
0.7845	Intermediate Similarity	NPC138372
0.7845	Intermediate Similarity	NPC255450
0.7845	Intermediate Similarity	NPC277583
0.7845	Intermediate Similarity	NPC266728
0.7845	Intermediate Similarity	NPC49492
0.7845	Intermediate Similarity	NPC148458
0.7845	Intermediate Similarity	NPC170692
0.784	Intermediate Similarity	NPC471234
0.7833	Intermediate Similarity	NPC11895
0.783	Intermediate Similarity	NPC36954
0.7826	Intermediate Similarity	NPC194100
0.7826	Intermediate Similarity	NPC469454
0.7826	Intermediate Similarity	NPC469463
0.7826	Intermediate Similarity	NPC469496
0.7823	Intermediate Similarity	NPC471855
0.7818	Intermediate Similarity	NPC110989
0.7818	Intermediate Similarity	NPC475321
0.7815	Intermediate Similarity	NPC473228
0.7815	Intermediate Similarity	NPC67569
0.7815	Intermediate Similarity	NPC470829
0.781	Intermediate Similarity	NPC476300
0.781	Intermediate Similarity	NPC475912
0.7807	Intermediate Similarity	NPC179798
0.7807	Intermediate Similarity	NPC304180
0.7807	Intermediate Similarity	NPC317107
0.7807	Intermediate Similarity	NPC71680
0.7805	Intermediate Similarity	NPC231529
0.7798	Intermediate Similarity	NPC471401
0.7798	Intermediate Similarity	NPC171759
0.7798	Intermediate Similarity	NPC476270
0.7798	Intermediate Similarity	NPC477950
0.7797	Intermediate Similarity	NPC9674
0.7797	Intermediate Similarity	NPC61520
0.7797	Intermediate Similarity	NPC19028
0.7788	Intermediate Similarity	NPC304495
0.7788	Intermediate Similarity	NPC477102
0.7787	Intermediate Similarity	NPC473265
0.7787	Intermediate Similarity	NPC473253
0.7778	Intermediate Similarity	NPC83895
0.7778	Intermediate Similarity	NPC261377
0.7778	Intermediate Similarity	NPC255592
0.7778	Intermediate Similarity	NPC473326
0.7778	Intermediate Similarity	NPC308567
0.7778	Intermediate Similarity	NPC239273
0.7778	Intermediate Similarity	NPC187761
0.7769	Intermediate Similarity	NPC8369
0.7769	Intermediate Similarity	NPC8374
0.7768	Intermediate Similarity	NPC80338
0.7768	Intermediate Similarity	NPC148270
0.7768	Intermediate Similarity	NPC197813
0.7759	Intermediate Similarity	NPC471398
0.7759	Intermediate Similarity	NPC474181
0.7759	Intermediate Similarity	NPC326542
0.7757	Intermediate Similarity	NPC18019
0.7757	Intermediate Similarity	NPC24956
0.7757	Intermediate Similarity	NPC279621
0.775	Intermediate Similarity	NPC170538
0.7748	Intermediate Similarity	NPC146731
0.7748	Intermediate Similarity	NPC472748
0.7748	Intermediate Similarity	NPC474741
0.7748	Intermediate Similarity	NPC100487
0.7748	Intermediate Similarity	NPC296950
0.7748	Intermediate Similarity	NPC258532
0.7748	Intermediate Similarity	NPC203659
0.7742	Intermediate Similarity	NPC173347
0.7739	Intermediate Similarity	NPC221144
0.7739	Intermediate Similarity	NPC475524
0.7739	Intermediate Similarity	NPC241477
0.7739	Intermediate Similarity	NPC100267
0.7736	Intermediate Similarity	NPC71589
0.7731	Intermediate Similarity	NPC474370
0.7727	Intermediate Similarity	NPC118405
0.7727	Intermediate Similarity	NPC476126
0.7727	Intermediate Similarity	NPC225353
0.7727	Intermediate Similarity	NPC476235
0.7727	Intermediate Similarity	NPC78127
0.7727	Intermediate Similarity	NPC473928
0.7727	Intermediate Similarity	NPC49393
0.7727	Intermediate Similarity	NPC471757

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 NPC50223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1665
0.2-0.3	3826
0.3-0.4	2324
0.4-0.5	668
0.5-0.6	242
0.6-0.7	205
0.7-0.8	40
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
0.7788	Intermediate Similarity	NPD6698	Approved
0.7788	Intermediate Similarity	NPD46	Approved
0.7731	Intermediate Similarity	NPD6319	Approved
0.7719	Intermediate Similarity	NPD6371	Approved
0.7586	Intermediate Similarity	NPD6053	Discontinued
0.7561	Intermediate Similarity	NPD7507	Approved
0.7544	Intermediate Similarity	NPD6686	Approved
0.7521	Intermediate Similarity	NPD4632	Approved
0.7479	Intermediate Similarity	NPD7115	Discovery
0.7456	Intermediate Similarity	NPD6412	Phase 2
0.7456	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD8297	Approved
0.7381	Intermediate Similarity	NPD7319	Approved
0.7368	Intermediate Similarity	NPD6008	Approved
0.735	Intermediate Similarity	NPD6649	Approved
0.735	Intermediate Similarity	NPD6650	Approved
0.7328	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6372	Approved
0.7328	Intermediate Similarity	NPD6373	Approved
0.7304	Intermediate Similarity	NPD5697	Approved
0.7265	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6881	Approved
0.7241	Intermediate Similarity	NPD6899	Approved
0.7217	Intermediate Similarity	NPD5739	Approved
0.7217	Intermediate Similarity	NPD6675	Approved
0.7217	Intermediate Similarity	NPD7128	Approved
0.7217	Intermediate Similarity	NPD6402	Approved
0.72	Intermediate Similarity	NPD7492	Approved
0.719	Intermediate Similarity	NPD6009	Approved
0.7179	Intermediate Similarity	NPD6013	Approved
0.7179	Intermediate Similarity	NPD6012	Approved
0.7179	Intermediate Similarity	NPD6014	Approved
0.7155	Intermediate Similarity	NPD5701	Approved
0.7154	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD6616	Approved
0.713	Intermediate Similarity	NPD7838	Discovery
0.713	Intermediate Similarity	NPD5785	Approved
0.712	Intermediate Similarity	NPD7604	Phase 2
0.7119	Intermediate Similarity	NPD7290	Approved
0.7119	Intermediate Similarity	NPD4634	Approved
0.7119	Intermediate Similarity	NPD6883	Approved
0.7119	Intermediate Similarity	NPD7102	Approved
0.7097	Intermediate Similarity	NPD5983	Phase 2
0.7097	Intermediate Similarity	NPD6016	Approved
0.7097	Intermediate Similarity	NPD7503	Approved
0.7097	Intermediate Similarity	NPD6015	Approved
0.7094	Intermediate Similarity	NPD7320	Approved
0.7094	Intermediate Similarity	NPD6011	Approved
0.7087	Intermediate Similarity	NPD7078	Approved
0.708	Intermediate Similarity	NPD7639	Approved
0.708	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD6847	Approved
0.7059	Intermediate Similarity	NPD6869	Approved
0.7059	Intermediate Similarity	NPD6617	Approved
0.7059	Intermediate Similarity	NPD8130	Phase 1
0.7054	Intermediate Similarity	NPD6083	Phase 2
0.7054	Intermediate Similarity	NPD6084	Phase 2
0.704	Intermediate Similarity	NPD5988	Approved
0.704	Intermediate Similarity	NPD6370	Approved
0.7031	Intermediate Similarity	NPD7736	Approved
0.7027	Intermediate Similarity	NPD5695	Phase 3
0.7027	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6435	Approved
0.7016	Intermediate Similarity	NPD6059	Approved
0.7009	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7260	Phase 2
0.6992	Remote Similarity	NPD7327	Approved
0.6992	Remote Similarity	NPD7328	Approved
0.6991	Remote Similarity	NPD5696	Approved
0.6981	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.696	Remote Similarity	NPD8033	Approved
0.6957	Remote Similarity	NPD5211	Phase 2
0.6953	Remote Similarity	NPD8293	Discontinued
0.6935	Remote Similarity	NPD7516	Approved
0.693	Remote Similarity	NPD5286	Approved
0.693	Remote Similarity	NPD5285	Approved
0.693	Remote Similarity	NPD4696	Approved
0.6903	Remote Similarity	NPD4755	Approved
0.6881	Remote Similarity	NPD1695	Approved
0.688	Remote Similarity	NPD8377	Approved
0.688	Remote Similarity	NPD8294	Approved
0.6875	Remote Similarity	NPD6336	Discontinued
0.6842	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4225	Approved
0.6838	Remote Similarity	NPD5141	Approved
0.6829	Remote Similarity	NPD6274	Approved
0.6827	Remote Similarity	NPD5368	Approved
0.6825	Remote Similarity	NPD8296	Approved
0.6825	Remote Similarity	NPD8517	Approved
0.6825	Remote Similarity	NPD8335	Approved
0.6825	Remote Similarity	NPD8516	Approved
0.6825	Remote Similarity	NPD8513	Phase 3
0.6825	Remote Similarity	NPD8378	Approved
0.6825	Remote Similarity	NPD8379	Approved
0.6825	Remote Similarity	NPD8380	Approved
0.6825	Remote Similarity	NPD8515	Approved
0.6822	Remote Similarity	NPD1694	Approved
0.681	Remote Similarity	NPD5224	Approved
0.681	Remote Similarity	NPD5225	Approved
0.681	Remote Similarity	NPD5226	Approved
0.681	Remote Similarity	NPD4633	Approved
0.6807	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4700	Approved
0.6777	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6409	Approved
0.6759	Remote Similarity	NPD7334	Approved
0.6759	Remote Similarity	NPD6684	Approved
0.6759	Remote Similarity	NPD5330	Approved
0.6759	Remote Similarity	NPD7521	Approved
0.6759	Remote Similarity	NPD7146	Approved
0.6757	Remote Similarity	NPD5281	Approved
0.6757	Remote Similarity	NPD5284	Approved
0.6757	Remote Similarity	NPD5693	Phase 1
0.6757	Remote Similarity	NPD7983	Approved
0.6752	Remote Similarity	NPD5174	Approved
0.6752	Remote Similarity	NPD5175	Approved
0.6729	Remote Similarity	NPD3666	Approved
0.6729	Remote Similarity	NPD3665	Phase 1
0.6729	Remote Similarity	NPD3133	Approved
0.6727	Remote Similarity	NPD4753	Phase 2
0.6726	Remote Similarity	NPD5210	Approved
0.6726	Remote Similarity	NPD4629	Approved
0.6724	Remote Similarity	NPD5344	Discontinued
0.6724	Remote Similarity	NPD5223	Approved
0.6719	Remote Similarity	NPD8328	Phase 3
0.6696	Remote Similarity	NPD6399	Phase 3
0.6692	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.664	Remote Similarity	NPD6317	Approved
0.6639	Remote Similarity	NPD4768	Approved
0.6639	Remote Similarity	NPD4767	Approved
0.6637	Remote Similarity	NPD5282	Discontinued
0.6636	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6903	Approved
0.6606	Remote Similarity	NPD5786	Approved
0.6606	Remote Similarity	NPD4249	Approved
0.6589	Remote Similarity	NPD7642	Approved
0.6587	Remote Similarity	NPD6314	Approved
0.6587	Remote Similarity	NPD6335	Approved
0.6587	Remote Similarity	NPD6313	Approved
0.6579	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD8074	Phase 3
0.6562	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5248	Approved
0.6557	Remote Similarity	NPD5249	Phase 3
0.6557	Remote Similarity	NPD5251	Approved
0.6557	Remote Similarity	NPD5250	Approved
0.6557	Remote Similarity	NPD5247	Approved
0.6549	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD4202	Approved
0.6549	Remote Similarity	NPD5778	Approved
0.6545	Remote Similarity	NPD4251	Approved
0.6545	Remote Similarity	NPD4250	Approved
0.6542	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5128	Approved
0.6525	Remote Similarity	NPD7632	Discontinued
0.6515	Remote Similarity	NPD6033	Approved
0.6514	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4819	Approved
0.6509	Remote Similarity	NPD4822	Approved
0.6509	Remote Similarity	NPD4821	Approved
0.6509	Remote Similarity	NPD4820	Approved
0.6509	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4754	Approved
0.6462	Remote Similarity	NPD7830	Approved
0.6462	Remote Similarity	NPD7829	Approved
0.646	Remote Similarity	NPD6411	Approved
0.646	Remote Similarity	NPD6079	Approved
0.6455	Remote Similarity	NPD3618	Phase 1
0.6449	Remote Similarity	NPD5369	Approved
0.6434	Remote Similarity	NPD6909	Approved
0.6434	Remote Similarity	NPD6908	Approved
0.6429	Remote Similarity	NPD6904	Approved
0.6429	Remote Similarity	NPD6080	Approved
0.6429	Remote Similarity	NPD6673	Approved
0.6429	Remote Similarity	NPD5328	Approved
0.6418	Remote Similarity	NPD5956	Approved
0.6406	Remote Similarity	NPD4522	Approved
0.6389	Remote Similarity	NPD4269	Approved
0.6389	Remote Similarity	NPD4223	Phase 3
0.6389	Remote Similarity	NPD4270	Approved
0.6389	Remote Similarity	NPD4221	Approved
0.6379	Remote Similarity	NPD5222	Approved
0.6379	Remote Similarity	NPD4697	Phase 3
0.6379	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5221	Approved
0.6377	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5692	Phase 3
0.6372	Remote Similarity	NPD5207	Approved
0.6371	Remote Similarity	NPD5215	Approved
0.6371	Remote Similarity	NPD5217	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