NPASS Compound

Structure

NPC476007 OpenBabel07101718222D 23 24 0 0 1 0 0 0 0 0999 V2000 3.1656 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4088 0.6784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9227 -2.7470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9227 -1.7470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -3.6479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 -2.7470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -3.6479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -4.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -4.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -0.8460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -0.8460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 -1.7470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 -2.7470 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1906 -1.7470 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9749 -0.2225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0567 -2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.4940 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4088 0.6784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -5.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 9 2 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 9 20 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 14 18 1 0 0 0 0 15 8 1 1 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 12 1 6 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 1 0 0 0 18 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	3.56
LogD:	2.982
LogS:	-4.513
# Rotatable Bonds:	0
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	4.516
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.631
MDCK Permeability:	1.5050660294946283e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.314
Plasma Protein Binding (PPB):	92.16181182861328%
Volume Distribution (VD):	1.479
Pgp-substrate:	4.828838348388672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.285
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.857
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.832
CYP2C9-substrate:	0.671
CYP2D6-inhibitor:	0.869
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.684
CYP3A4-substrate:	0.409

ADMET: Excretion

Clearance (CL):	9.16
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.609
Drug-inuced Liver Injury (DILI):	0.264
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.954
Carcinogencity:	0.256
Eye Corrosion:	0.351
Eye Irritation:	0.342
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC476007

Natural Product ID:	NPC476007
*Common Name:**	Agroskerin
IUPAC Name:	(1R,5E,8E,10S,12E,14R)-4,10-dihydroxy-4,8,12,15,15-pentamethylbicyclo[12.1.0]pentadeca-5,8,12-trien-11-one
Synonyms:	Agroskerin
Standard InCHIKey:	DGENOXRJSTZHMV-KUOLMVOASA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13-7-6-9-20(5,23)10-8-15-16(19(15,3)4)12-14(2)18(22)17(21)11-13/h6,9,11-12,15-17,21,23H,7-8,10H2,1-5H3/b9-6+,13-11+,14-12+/t15-,16-,17+,20?/m1/s1
SMILES:	CC1=CC(C(=O)C(=CC2C(C2(C)C)CCC(C=CC1)(C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521362
PubChem CID:	44559808
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000008] Cembrane diterpenoids

*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
NPO17157	Agrostistachys hookeri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3373221]
NPO17157	Agrostistachys hookeri	Species	Euphorbiaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.4	ug ml-1	PMID[567387]

☑ 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 NPC476007 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	188
0.1-0.2	1374
0.2-0.3	6246
0.3-0.4	16691
0.4-0.5	9022
0.5-0.6	6552
0.6-0.7	2416
0.7-0.8	195
0.8-0.85	6
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC474885
0.9155	High Similarity	NPC286154
0.9028	High Similarity	NPC474884
0.8289	Intermediate Similarity	NPC227814
0.8289	Intermediate Similarity	NPC144995
0.8101	Intermediate Similarity	NPC475994
0.8025	Intermediate Similarity	NPC112868
0.7975	Intermediate Similarity	NPC211279
0.7927	Intermediate Similarity	NPC145963
0.7875	Intermediate Similarity	NPC478122
0.7875	Intermediate Similarity	NPC231739
0.7867	Intermediate Similarity	NPC117804
0.7857	Intermediate Similarity	NPC96621
0.7841	Intermediate Similarity	NPC125180
0.7792	Intermediate Similarity	NPC95863
0.7791	Intermediate Similarity	NPC60765
0.7765	Intermediate Similarity	NPC472974
0.775	Intermediate Similarity	NPC149550
0.775	Intermediate Similarity	NPC203403
0.775	Intermediate Similarity	NPC85105
0.7738	Intermediate Similarity	NPC472326
0.7711	Intermediate Similarity	NPC93590
0.7701	Intermediate Similarity	NPC170775
0.7692	Intermediate Similarity	NPC186042
0.7654	Intermediate Similarity	NPC321180
0.7647	Intermediate Similarity	NPC11804
0.7625	Intermediate Similarity	NPC469646
0.76	Intermediate Similarity	NPC267027
0.759	Intermediate Similarity	NPC6663
0.7568	Intermediate Similarity	NPC300593
0.7564	Intermediate Similarity	NPC471662
0.7561	Intermediate Similarity	NPC19900
0.7561	Intermediate Similarity	NPC308038
0.7561	Intermediate Similarity	NPC136033
0.7558	Intermediate Similarity	NPC194417
0.7532	Intermediate Similarity	NPC471560
0.7532	Intermediate Similarity	NPC10758
0.7532	Intermediate Similarity	NPC250928
0.7529	Intermediate Similarity	NPC476412
0.75	Intermediate Similarity	NPC158411
0.75	Intermediate Similarity	NPC106613
0.75	Intermediate Similarity	NPC122239
0.75	Intermediate Similarity	NPC474011
0.75	Intermediate Similarity	NPC38796
0.747	Intermediate Similarity	NPC471514
0.747	Intermediate Similarity	NPC471656
0.7468	Intermediate Similarity	NPC275098
0.7468	Intermediate Similarity	NPC329763
0.7465	Intermediate Similarity	NPC71755
0.7442	Intermediate Similarity	NPC476426
0.7442	Intermediate Similarity	NPC474853
0.7442	Intermediate Similarity	NPC79573
0.7442	Intermediate Similarity	NPC179006
0.7439	Intermediate Similarity	NPC62336
0.7439	Intermediate Similarity	NPC192006
0.7412	Intermediate Similarity	NPC477785
0.7412	Intermediate Similarity	NPC79945
0.7412	Intermediate Similarity	NPC477786
0.7412	Intermediate Similarity	NPC477784
0.7412	Intermediate Similarity	NPC161045
0.7407	Intermediate Similarity	NPC250621
0.7407	Intermediate Similarity	NPC263582
0.7407	Intermediate Similarity	NPC271070
0.7407	Intermediate Similarity	NPC470525
0.7407	Intermediate Similarity	NPC471658
0.7386	Intermediate Similarity	NPC229612
0.7386	Intermediate Similarity	NPC7280
0.7381	Intermediate Similarity	NPC159148
0.7381	Intermediate Similarity	NPC325031
0.7375	Intermediate Similarity	NPC206875
0.7375	Intermediate Similarity	NPC471659
0.7375	Intermediate Similarity	NPC215050
0.7375	Intermediate Similarity	NPC78527
0.7368	Intermediate Similarity	NPC118405
0.7363	Intermediate Similarity	NPC217624
0.7363	Intermediate Similarity	NPC181393
0.7356	Intermediate Similarity	NPC94666
0.7356	Intermediate Similarity	NPC202394
0.7349	Intermediate Similarity	NPC470429
0.7349	Intermediate Similarity	NPC170394
0.7349	Intermediate Similarity	NPC281138
0.7342	Intermediate Similarity	NPC67076
0.7342	Intermediate Similarity	NPC319163
0.7333	Intermediate Similarity	NPC309300
0.7333	Intermediate Similarity	NPC219874
0.7326	Intermediate Similarity	NPC33913
0.7317	Intermediate Similarity	NPC74995
0.7317	Intermediate Similarity	NPC86917
0.7317	Intermediate Similarity	NPC276769
0.7317	Intermediate Similarity	NPC470428
0.7317	Intermediate Similarity	NPC471061
0.7308	Intermediate Similarity	NPC304690
0.7308	Intermediate Similarity	NPC74722
0.7303	Intermediate Similarity	NPC472973
0.7303	Intermediate Similarity	NPC257485
0.7297	Intermediate Similarity	NPC228574
0.7297	Intermediate Similarity	NPC294304
0.7294	Intermediate Similarity	NPC92226
0.7294	Intermediate Similarity	NPC103486
0.7294	Intermediate Similarity	NPC279186
0.7284	Intermediate Similarity	NPC114236
0.7283	Intermediate Similarity	NPC476245
0.7273	Intermediate Similarity	NPC136813
0.7273	Intermediate Similarity	NPC45957
0.7273	Intermediate Similarity	NPC287079
0.7273	Intermediate Similarity	NPC471657
0.7273	Intermediate Similarity	NPC96962
0.7273	Intermediate Similarity	NPC477791
0.7273	Intermediate Similarity	NPC73603
0.7273	Intermediate Similarity	NPC114651
0.7262	Intermediate Similarity	NPC45495
0.7262	Intermediate Similarity	NPC172013
0.7262	Intermediate Similarity	NPC281880
0.726	Intermediate Similarity	NPC475931
0.7253	Intermediate Similarity	NPC474736
0.725	Intermediate Similarity	NPC130665
0.725	Intermediate Similarity	NPC323437
0.725	Intermediate Similarity	NPC29542
0.725	Intermediate Similarity	NPC201562
0.7241	Intermediate Similarity	NPC109528
0.7241	Intermediate Similarity	NPC261380
0.7237	Intermediate Similarity	NPC308844
0.7237	Intermediate Similarity	NPC61503
0.7237	Intermediate Similarity	NPC19569
0.7229	Intermediate Similarity	NPC476949
0.7229	Intermediate Similarity	NPC471409
0.7229	Intermediate Similarity	NPC172066
0.7229	Intermediate Similarity	NPC297996
0.7229	Intermediate Similarity	NPC275494
0.7222	Intermediate Similarity	NPC38952
0.7222	Intermediate Similarity	NPC182136
0.7222	Intermediate Similarity	NPC469368
0.7222	Intermediate Similarity	NPC145666
0.7215	Intermediate Similarity	NPC34834
0.7215	Intermediate Similarity	NPC318766
0.7209	Intermediate Similarity	NPC57370
0.7209	Intermediate Similarity	NPC474809
0.72	Intermediate Similarity	NPC473759
0.72	Intermediate Similarity	NPC474155
0.72	Intermediate Similarity	NPC473508
0.7195	Intermediate Similarity	NPC167873
0.7195	Intermediate Similarity	NPC310643
0.7195	Intermediate Similarity	NPC265588
0.7195	Intermediate Similarity	NPC1973
0.7191	Intermediate Similarity	NPC53454
0.7188	Intermediate Similarity	NPC87351
0.7179	Intermediate Similarity	NPC224532
0.7179	Intermediate Similarity	NPC305698
0.7179	Intermediate Similarity	NPC167527
0.7179	Intermediate Similarity	NPC469688
0.7179	Intermediate Similarity	NPC45264
0.7179	Intermediate Similarity	NPC471238
0.7176	Intermediate Similarity	NPC6434
0.7176	Intermediate Similarity	NPC136150
0.7176	Intermediate Similarity	NPC470298
0.7174	Intermediate Similarity	NPC299100
0.7174	Intermediate Similarity	NPC65829
0.7174	Intermediate Similarity	NPC472977
0.7174	Intermediate Similarity	NPC476186
0.7174	Intermediate Similarity	NPC472976
0.7162	Intermediate Similarity	NPC99487
0.7162	Intermediate Similarity	NPC66020
0.716	Intermediate Similarity	NPC469691
0.716	Intermediate Similarity	NPC167049
0.716	Intermediate Similarity	NPC22134
0.7159	Intermediate Similarity	NPC261721
0.7159	Intermediate Similarity	NPC472985
0.7159	Intermediate Similarity	NPC472986
0.7143	Intermediate Similarity	NPC7232
0.7143	Intermediate Similarity	NPC197089
0.7143	Intermediate Similarity	NPC110923
0.7143	Intermediate Similarity	NPC152061
0.7143	Intermediate Similarity	NPC74296
0.7143	Intermediate Similarity	NPC325869
0.7143	Intermediate Similarity	NPC472978
0.7143	Intermediate Similarity	NPC475806
0.7128	Intermediate Similarity	NPC471916
0.7126	Intermediate Similarity	NPC160517
0.7126	Intermediate Similarity	NPC7927
0.7126	Intermediate Similarity	NPC230527
0.7126	Intermediate Similarity	NPC186155
0.7126	Intermediate Similarity	NPC472265
0.7126	Intermediate Similarity	NPC78673
0.7126	Intermediate Similarity	NPC302360
0.7126	Intermediate Similarity	NPC82297
0.7125	Intermediate Similarity	NPC477792
0.7125	Intermediate Similarity	NPC471272
0.7125	Intermediate Similarity	NPC471660
0.7123	Intermediate Similarity	NPC181872
0.7123	Intermediate Similarity	NPC226848
0.7123	Intermediate Similarity	NPC155025
0.7113	Intermediate Similarity	NPC111323
0.7113	Intermediate Similarity	NPC131366
0.7113	Intermediate Similarity	NPC311612
0.7111	Intermediate Similarity	NPC314727
0.7111	Intermediate Similarity	NPC146554
0.7111	Intermediate Similarity	NPC50488
0.7111	Intermediate Similarity	NPC477215
0.7111	Intermediate Similarity	NPC472983
0.7111	Intermediate Similarity	NPC476388

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 NPC476007 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1967
0.2-0.3	4098
0.3-0.4	2096
0.4-0.5	478
0.5-0.6	256
0.6-0.7	68
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7647	Intermediate Similarity	NPD1696	Phase 3
0.7059	Intermediate Similarity	NPD4695	Discontinued
0.7045	Intermediate Similarity	NPD5363	Approved
0.7033	Intermediate Similarity	NPD5785	Approved
0.7024	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5279	Phase 3
0.6867	Remote Similarity	NPD8264	Approved
0.686	Remote Similarity	NPD4822	Approved
0.686	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4821	Approved
0.686	Remote Similarity	NPD4819	Approved
0.686	Remote Similarity	NPD4820	Approved
0.6842	Remote Similarity	NPD368	Approved
0.6837	Remote Similarity	NPD5211	Phase 2
0.6824	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5282	Discontinued
0.6782	Remote Similarity	NPD6902	Approved
0.6778	Remote Similarity	NPD4623	Approved
0.6778	Remote Similarity	NPD5690	Phase 2
0.6778	Remote Similarity	NPD4519	Discontinued
0.6747	Remote Similarity	NPD6926	Approved
0.6747	Remote Similarity	NPD6924	Approved
0.6744	Remote Similarity	NPD4195	Approved
0.6742	Remote Similarity	NPD3665	Phase 1
0.6742	Remote Similarity	NPD3133	Approved
0.6742	Remote Similarity	NPD3666	Approved
0.6739	Remote Similarity	NPD4753	Phase 2
0.6737	Remote Similarity	NPD4629	Approved
0.6737	Remote Similarity	NPD5210	Approved
0.6705	Remote Similarity	NPD3667	Approved
0.6705	Remote Similarity	NPD5209	Approved
0.6705	Remote Similarity	NPD4270	Approved
0.6705	Remote Similarity	NPD4269	Approved
0.67	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6633	Remote Similarity	NPD4696	Approved
0.6633	Remote Similarity	NPD5285	Approved
0.6633	Remote Similarity	NPD5286	Approved
0.6629	Remote Similarity	NPD5332	Approved
0.6629	Remote Similarity	NPD5362	Discontinued
0.6629	Remote Similarity	NPD5331	Approved
0.6628	Remote Similarity	NPD4268	Approved
0.6628	Remote Similarity	NPD4271	Approved
0.6598	Remote Similarity	NPD5173	Approved
0.6596	Remote Similarity	NPD6079	Approved
0.6593	Remote Similarity	NPD3618	Phase 1
0.6591	Remote Similarity	NPD4790	Discontinued
0.6588	Remote Similarity	NPD6933	Approved
0.6582	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5223	Approved
0.6562	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4786	Approved
0.6556	Remote Similarity	NPD4197	Approved
0.6552	Remote Similarity	NPD6929	Approved
0.6538	Remote Similarity	NPD6371	Approved
0.6531	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD5225	Approved
0.65	Remote Similarity	NPD5226	Approved
0.65	Remote Similarity	NPD4633	Approved
0.65	Remote Similarity	NPD7331	Phase 2
0.65	Remote Similarity	NPD5224	Approved
0.6486	Remote Similarity	NPD342	Phase 1
0.6484	Remote Similarity	NPD5329	Approved
0.6477	Remote Similarity	NPD4252	Approved
0.6477	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7154	Phase 3
0.6444	Remote Similarity	NPD6695	Phase 3
0.6444	Remote Similarity	NPD6110	Phase 1
0.6437	Remote Similarity	NPD7145	Approved
0.6436	Remote Similarity	NPD5174	Approved
0.6436	Remote Similarity	NPD5175	Approved
0.6429	Remote Similarity	NPD4755	Approved
0.6429	Remote Similarity	NPD4732	Discontinued
0.6413	Remote Similarity	NPD5280	Approved
0.6413	Remote Similarity	NPD5786	Approved
0.6413	Remote Similarity	NPD4694	Approved
0.6404	Remote Similarity	NPD5369	Approved
0.64	Remote Similarity	NPD5344	Discontinued
0.6395	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7144	Approved
0.6386	Remote Similarity	NPD7143	Approved
0.6383	Remote Similarity	NPD5328	Approved
0.6375	Remote Similarity	NPD7341	Phase 2
0.6374	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4202	Approved
0.6344	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4221	Approved
0.6333	Remote Similarity	NPD4223	Phase 3
0.6329	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4697	Phase 3
0.6322	Remote Similarity	NPD4756	Discovery
0.6322	Remote Similarity	NPD6925	Approved
0.6322	Remote Similarity	NPD5776	Phase 2
0.6322	Remote Similarity	NPD6932	Approved
0.631	Remote Similarity	NPD7151	Approved
0.631	Remote Similarity	NPD7150	Approved
0.631	Remote Similarity	NPD7152	Approved
0.6304	Remote Similarity	NPD6893	Approved
0.6304	Remote Similarity	NPD1694	Approved
0.63	Remote Similarity	NPD4700	Approved
0.6292	Remote Similarity	NPD7509	Discontinued
0.6279	Remote Similarity	NPD6942	Approved
0.6279	Remote Similarity	NPD7339	Approved
0.6277	Remote Similarity	NPD4518	Approved
0.6265	Remote Similarity	NPD6923	Approved
0.6265	Remote Similarity	NPD6922	Approved
0.6263	Remote Similarity	NPD6083	Phase 2
0.6263	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD3617	Approved
0.625	Remote Similarity	NPD5697	Approved
0.6224	Remote Similarity	NPD5695	Phase 3
0.6222	Remote Similarity	NPD6898	Phase 1
0.6203	Remote Similarity	NPD4193	Approved
0.6203	Remote Similarity	NPD4194	Approved
0.6203	Remote Similarity	NPD4192	Approved
0.6203	Remote Similarity	NPD4191	Approved
0.62	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4729	Approved
0.619	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD4730	Approved
0.619	Remote Similarity	NPD6881	Approved
0.619	Remote Similarity	NPD6899	Approved
0.6186	Remote Similarity	NPD5133	Approved
0.6186	Remote Similarity	NPD5779	Approved
0.6186	Remote Similarity	NPD5778	Approved
0.6184	Remote Similarity	NPD4219	Approved
0.6182	Remote Similarity	NPD7115	Discovery
0.617	Remote Similarity	NPD7524	Approved
0.617	Remote Similarity	NPD7750	Discontinued
0.6154	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD46	Approved
0.6146	Remote Similarity	NPD6698	Approved
0.6139	Remote Similarity	NPD7640	Approved
0.6139	Remote Similarity	NPD6648	Approved
0.6139	Remote Similarity	NPD7639	Approved
0.6132	Remote Similarity	NPD6014	Approved
0.6132	Remote Similarity	NPD6012	Approved
0.6132	Remote Similarity	NPD6013	Approved
0.6117	Remote Similarity	NPD4754	Approved
0.6111	Remote Similarity	NPD5368	Approved
0.6111	Remote Similarity	NPD7525	Registered
0.6098	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3704	Approved
0.6087	Remote Similarity	NPD4788	Approved
0.6082	Remote Similarity	NPD6411	Approved
0.6076	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5250	Approved
0.6075	Remote Similarity	NPD6883	Approved
0.6075	Remote Similarity	NPD5249	Phase 3
0.6075	Remote Similarity	NPD4634	Approved
0.6075	Remote Similarity	NPD5251	Approved
0.6075	Remote Similarity	NPD7290	Approved
0.6075	Remote Similarity	NPD7102	Approved
0.6075	Remote Similarity	NPD5169	Approved
0.6075	Remote Similarity	NPD5135	Approved
0.6075	Remote Similarity	NPD5248	Approved
0.6075	Remote Similarity	NPD5247	Approved
0.6075	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4689	Approved
0.6064	Remote Similarity	NPD4690	Approved
0.6064	Remote Similarity	NPD5205	Approved
0.6064	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4138	Approved
0.6064	Remote Similarity	NPD4688	Approved
0.6064	Remote Similarity	NPD4249	Approved
0.6064	Remote Similarity	NPD4693	Phase 3
0.6049	Remote Similarity	NPD3197	Phase 1
0.6042	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7638	Approved
0.604	Remote Similarity	NPD5696	Approved
0.604	Remote Similarity	NPD5290	Discontinued
0.6038	Remote Similarity	NPD5128	Approved
0.6038	Remote Similarity	NPD5168	Approved
0.6022	Remote Similarity	NPD3668	Phase 3
0.6019	Remote Similarity	NPD5215	Approved
0.6019	Remote Similarity	NPD5216	Approved
0.6019	Remote Similarity	NPD6650	Approved
0.6019	Remote Similarity	NPD5127	Approved
0.6019	Remote Similarity	NPD8130	Phase 1
0.6019	Remote Similarity	NPD6847	Approved
0.6019	Remote Similarity	NPD6649	Approved
0.6019	Remote Similarity	NPD6869	Approved
0.6019	Remote Similarity	NPD5217	Approved
0.6019	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD7645	Phase 2
0.6	Remote Similarity	NPD6683	Phase 2
0.6	Remote Similarity	NPD6675	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