NPASS Compound

Structure

CID322188 OpenBabel06191716162D 36 38 0 0 1 0 0 0 0 0999 V2000 -0.0377 8.2131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2834 3.5868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1078 -0.6729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5007 2.1618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1636 -1.8703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7395 1.8297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2138 7.2743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3447 3.3352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4734 6.5871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9543 0.7445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6219 1.3202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6833 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6833 0.9719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3324 -0.9132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9571 3.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6219 0.1688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4712 2.1618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9571 1.3202 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8416 -0.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6575 4.0224 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8416 -0.4859 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2218 5.6484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9571 0.1688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6247 0.7445 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9719 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2812 3.7709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3324 -0.9132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8416 1.4578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9289 3.0035 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6833 -0.9719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7169 5.3969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9684 4.4581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0769 -1.5379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9090 4.9612 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 0.5328 2.8322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 16 2 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 28 1 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 17 4 1 1 0 0 0 18 17 1 1 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 19 30 2 0 0 0 0 20 26 1 0 0 0 0 20 34 1 0 0 0 0 21 27 1 1 0 0 0 21 35 1 0 0 0 0 22 31 2 0 0 0 0 22 34 1 0 0 0 0 23 16 1 6 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 28 1 0 0 0 0 25 35 1 0 0 0 0 26 32 2 0 0 0 0 26 36 1 0 0 0 0 27 33 1 0 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.3
Volume:	526.951
LogP:	3.628
LogD:	2.975
LogS:	-3.918
# Rotatable Bonds:	10
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	5.789
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.754
MDCK Permeability:	8.371676813112572e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.082
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.563

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	90.86389923095703%
Volume Distribution (VD):	0.852
Pgp-substrate:	2.8755593299865723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.724
CYP3A4-substrate:	0.682

ADMET: Excretion

Clearance (CL):	5.652
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.899
Drug-inuced Liver Injury (DILI):	0.836
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.146
Skin Sensitization:	0.535
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.05

Download Data

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

Natural Product: NPC322188

Natural Product ID:	NPC322188
*Common Name:**	Hirsutalin F
IUPAC Name:	n.a.
Synonyms:	Hirsutalin F
Standard InCHIKey:	HURFLECHLMMVAG-SVXRWCJSSA-N
Standard InCHI:	InChI=1S/C28H44O8/c1-7-9-22(31)34-20(8-2)26(32)36-28(6)13-12-21-27(5,33)14-19(30)23-16(3)10-11-18(17(4)15-29)24(23)25(28)35-21/h17-18,20-21,23-25,29,33H,3,7-15H2,1-2,4-6H3/t17-,18+,20?,21+,23+,24+,25+,27+,28+/m0/s1
SMILES:	CCCC(=O)OC(CC)C(=O)OC1(CCC2C(CC(=O)C3C(C1O2)C(CCC3=C)C(C)CO)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1631452
PubChem CID:	50900139
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO16112	Cladiella hirsuta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20979397]
NPO16112	Cladiella hirsuta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	29000.0	nM	PMID[561828]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	32000.0	nM	PMID[561828]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29000.0	nM	PMID[561828]

☑ 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 NPC322188 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	249
0.1-0.2	1853
0.2-0.3	6018
0.3-0.4	11175
0.4-0.5	11000
0.5-0.6	7561
0.6-0.7	4457
0.7-0.8	377
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8298	Intermediate Similarity	NPC65359
0.8269	Intermediate Similarity	NPC157476
0.8211	Intermediate Similarity	NPC329952
0.8173	Intermediate Similarity	NPC100908
0.8021	Intermediate Similarity	NPC469627
0.7961	Intermediate Similarity	NPC474101
0.7879	Intermediate Similarity	NPC39859
0.7879	Intermediate Similarity	NPC76862
0.7879	Intermediate Similarity	NPC158416
0.7879	Intermediate Similarity	NPC476009
0.7879	Intermediate Similarity	NPC470883
0.781	Intermediate Similarity	NPC289702
0.781	Intermediate Similarity	NPC208461
0.7778	Intermediate Similarity	NPC475900
0.7767	Intermediate Similarity	NPC277074
0.7767	Intermediate Similarity	NPC209298
0.7767	Intermediate Similarity	NPC122811
0.7723	Intermediate Similarity	NPC17183
0.7714	Intermediate Similarity	NPC176949
0.7714	Intermediate Similarity	NPC112780
0.7714	Intermediate Similarity	NPC201908
0.7714	Intermediate Similarity	NPC166993
0.77	Intermediate Similarity	NPC469528
0.77	Intermediate Similarity	NPC469369
0.77	Intermediate Similarity	NPC260223
0.7692	Intermediate Similarity	NPC470104
0.7684	Intermediate Similarity	NPC321812
0.7684	Intermediate Similarity	NPC322922
0.7677	Intermediate Similarity	NPC190294
0.7667	Intermediate Similarity	NPC474003
0.7664	Intermediate Similarity	NPC320383
0.7664	Intermediate Similarity	NPC137104
0.7664	Intermediate Similarity	NPC474786
0.766	Intermediate Similarity	NPC151176
0.766	Intermediate Similarity	NPC475963
0.766	Intermediate Similarity	NPC3464
0.7658	Intermediate Similarity	NPC297179
0.7658	Intermediate Similarity	NPC17772
0.7642	Intermediate Similarity	NPC151393
0.7642	Intermediate Similarity	NPC153587
0.7642	Intermediate Similarity	NPC273155
0.7636	Intermediate Similarity	NPC40632
0.7636	Intermediate Similarity	NPC16081
0.7636	Intermediate Similarity	NPC96312
0.7636	Intermediate Similarity	NPC251236
0.7636	Intermediate Similarity	NPC173686
0.7636	Intermediate Similarity	NPC328374
0.7629	Intermediate Similarity	NPC173926
0.7629	Intermediate Similarity	NPC77001
0.7629	Intermediate Similarity	NPC253618
0.7629	Intermediate Similarity	NPC474951
0.7624	Intermediate Similarity	NPC111348
0.7624	Intermediate Similarity	NPC328562
0.7624	Intermediate Similarity	NPC323421
0.7619	Intermediate Similarity	NPC200957
0.7619	Intermediate Similarity	NPC138908
0.7619	Intermediate Similarity	NPC292588
0.7615	Intermediate Similarity	NPC7921
0.7615	Intermediate Similarity	NPC208998
0.7609	Intermediate Similarity	NPC103634
0.7596	Intermediate Similarity	NPC469985
0.7589	Intermediate Similarity	NPC319570
0.7576	Intermediate Similarity	NPC199543
0.7573	Intermediate Similarity	NPC236585
0.7573	Intermediate Similarity	NPC252614
0.757	Intermediate Similarity	NPC131903
0.757	Intermediate Similarity	NPC16657
0.757	Intermediate Similarity	NPC204652
0.757	Intermediate Similarity	NPC274827
0.7568	Intermediate Similarity	NPC97908
0.7568	Intermediate Similarity	NPC122033
0.7568	Intermediate Similarity	NPC476713
0.7568	Intermediate Similarity	NPC476712
0.7568	Intermediate Similarity	NPC470854
0.7568	Intermediate Similarity	NPC474654
0.7568	Intermediate Similarity	NPC287343
0.7553	Intermediate Similarity	NPC239308
0.7549	Intermediate Similarity	NPC474793
0.7549	Intermediate Similarity	NPC471038
0.7547	Intermediate Similarity	NPC186054
0.7547	Intermediate Similarity	NPC471474
0.7545	Intermediate Similarity	NPC143268
0.7545	Intermediate Similarity	NPC45218
0.7545	Intermediate Similarity	NPC473798
0.7545	Intermediate Similarity	NPC323821
0.7545	Intermediate Similarity	NPC268238
0.7526	Intermediate Similarity	NPC255176
0.7525	Intermediate Similarity	NPC31645
0.7525	Intermediate Similarity	NPC256227
0.7525	Intermediate Similarity	NPC219353
0.7524	Intermediate Similarity	NPC301787
0.7523	Intermediate Similarity	NPC474927
0.7523	Intermediate Similarity	NPC317687
0.7522	Intermediate Similarity	NPC317635
0.7522	Intermediate Similarity	NPC329008
0.7521	Intermediate Similarity	NPC188291
0.75	Intermediate Similarity	NPC475491
0.75	Intermediate Similarity	NPC470776
0.75	Intermediate Similarity	NPC251310
0.75	Intermediate Similarity	NPC85391
0.75	Intermediate Similarity	NPC275990
0.75	Intermediate Similarity	NPC469626
0.75	Intermediate Similarity	NPC286347
0.7478	Intermediate Similarity	NPC91693
0.7478	Intermediate Similarity	NPC265557
0.7478	Intermediate Similarity	NPC18945
0.7478	Intermediate Similarity	NPC105926
0.7477	Intermediate Similarity	NPC476711
0.7477	Intermediate Similarity	NPC476710
0.7477	Intermediate Similarity	NPC63841
0.7477	Intermediate Similarity	NPC474734
0.7477	Intermediate Similarity	NPC473410
0.7477	Intermediate Similarity	NPC469984
0.7477	Intermediate Similarity	NPC190185
0.7477	Intermediate Similarity	NPC134869
0.7477	Intermediate Similarity	NPC152199
0.7477	Intermediate Similarity	NPC471094
0.7477	Intermediate Similarity	NPC235539
0.7477	Intermediate Similarity	NPC293850
0.7477	Intermediate Similarity	NPC213084
0.7476	Intermediate Similarity	NPC293890
0.7476	Intermediate Similarity	NPC470388
0.7476	Intermediate Similarity	NPC472972
0.7476	Intermediate Similarity	NPC267921
0.7475	Intermediate Similarity	NPC198054
0.7473	Intermediate Similarity	NPC469867
0.7456	Intermediate Similarity	NPC470779
0.7456	Intermediate Similarity	NPC75417
0.7455	Intermediate Similarity	NPC471252
0.7455	Intermediate Similarity	NPC49451
0.7455	Intermediate Similarity	NPC198539
0.7455	Intermediate Similarity	NPC94509
0.7453	Intermediate Similarity	NPC56656
0.7453	Intermediate Similarity	NPC222833
0.7453	Intermediate Similarity	NPC50535
0.7451	Intermediate Similarity	NPC124246
0.7451	Intermediate Similarity	NPC40812
0.7451	Intermediate Similarity	NPC236176
0.7449	Intermediate Similarity	NPC92974
0.7434	Intermediate Similarity	NPC180550
0.7434	Intermediate Similarity	NPC470777
0.7434	Intermediate Similarity	NPC475171
0.7434	Intermediate Similarity	NPC309780
0.7434	Intermediate Similarity	NPC6377
0.7434	Intermediate Similarity	NPC469945
0.7434	Intermediate Similarity	NPC214484
0.7434	Intermediate Similarity	NPC157868
0.7434	Intermediate Similarity	NPC35405
0.7434	Intermediate Similarity	NPC39211
0.7434	Intermediate Similarity	NPC208381
0.7434	Intermediate Similarity	NPC11551
0.7434	Intermediate Similarity	NPC472949
0.7434	Intermediate Similarity	NPC473884
0.7434	Intermediate Similarity	NPC114441
0.7431	Intermediate Similarity	NPC171888
0.7431	Intermediate Similarity	NPC470281
0.7431	Intermediate Similarity	NPC472003
0.7431	Intermediate Similarity	NPC146945
0.7431	Intermediate Similarity	NPC317107
0.7431	Intermediate Similarity	NPC213320
0.7431	Intermediate Similarity	NPC34315
0.7429	Intermediate Similarity	NPC225238
0.7429	Intermediate Similarity	NPC96217
0.7426	Intermediate Similarity	NPC248574
0.7414	Intermediate Similarity	NPC476729
0.7411	Intermediate Similarity	NPC224121
0.7411	Intermediate Similarity	NPC473590
0.7411	Intermediate Similarity	NPC146432
0.7411	Intermediate Similarity	NPC470778
0.7411	Intermediate Similarity	NPC470775
0.7411	Intermediate Similarity	NPC176513
0.7407	Intermediate Similarity	NPC42662
0.7407	Intermediate Similarity	NPC475922
0.7407	Intermediate Similarity	NPC27814
0.7404	Intermediate Similarity	NPC97435
0.7404	Intermediate Similarity	NPC46848
0.7404	Intermediate Similarity	NPC98225
0.74	Intermediate Similarity	NPC478036
0.74	Intermediate Similarity	NPC478037
0.74	Intermediate Similarity	NPC475788
0.7391	Intermediate Similarity	NPC476986
0.7391	Intermediate Similarity	NPC471965
0.7391	Intermediate Similarity	NPC312833
0.7391	Intermediate Similarity	NPC470905
0.7391	Intermediate Similarity	NPC162574
0.7387	Intermediate Similarity	NPC299849
0.7387	Intermediate Similarity	NPC18547
0.7387	Intermediate Similarity	NPC473898
0.7387	Intermediate Similarity	NPC474906
0.7383	Intermediate Similarity	NPC202524
0.7383	Intermediate Similarity	NPC251824
0.7383	Intermediate Similarity	NPC3316
0.7383	Intermediate Similarity	NPC86852
0.7383	Intermediate Similarity	NPC144854
0.7379	Intermediate Similarity	NPC255592
0.7379	Intermediate Similarity	NPC83895
0.7379	Intermediate Similarity	NPC469565
0.7379	Intermediate Similarity	NPC261377
0.7379	Intermediate Similarity	NPC26270
0.7379	Intermediate Similarity	NPC187761

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 NPC322188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	2435
0.2-0.3	3784
0.3-0.4	1675
0.4-0.5	592
0.5-0.6	295
0.6-0.7	125
0.7-0.8	2
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
0.781	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD8328	Phase 3
0.7257	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6319	Approved
0.7155	Intermediate Similarity	NPD6921	Approved
0.7129	Intermediate Similarity	NPD7983	Approved
0.6937	Remote Similarity	NPD6373	Approved
0.6937	Remote Similarity	NPD6372	Approved
0.6931	Remote Similarity	NPD6101	Approved
0.6931	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8297	Approved
0.6893	Remote Similarity	NPD5778	Approved
0.6893	Remote Similarity	NPD5779	Approved
0.6863	Remote Similarity	NPD6698	Approved
0.6863	Remote Similarity	NPD46	Approved
0.6847	Remote Similarity	NPD6686	Approved
0.6842	Remote Similarity	NPD4632	Approved
0.6833	Remote Similarity	NPD7492	Approved
0.6818	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6675	Approved
0.6818	Remote Similarity	NPD7128	Approved
0.6814	Remote Similarity	NPD6650	Approved
0.6814	Remote Similarity	NPD6649	Approved
0.6796	Remote Similarity	NPD6411	Approved
0.6786	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6054	Approved
0.678	Remote Similarity	NPD6059	Approved
0.6777	Remote Similarity	NPD6616	Approved
0.6757	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8293	Discontinued
0.6721	Remote Similarity	NPD7078	Approved
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6696	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6612	Remote Similarity	NPD7604	Phase 2
0.6609	Remote Similarity	NPD6882	Approved
0.6607	Remote Similarity	NPD6412	Phase 2
0.6607	Remote Similarity	NPD5697	Approved
0.6607	Remote Similarity	NPD5701	Approved
0.6583	Remote Similarity	NPD6015	Approved
0.6583	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6016	Approved
0.6583	Remote Similarity	NPD5983	Phase 2
0.6579	Remote Similarity	NPD7290	Approved
0.6579	Remote Similarity	NPD7102	Approved
0.6579	Remote Similarity	NPD6883	Approved
0.6571	Remote Similarity	NPD6399	Phase 3
0.6549	Remote Similarity	NPD6011	Approved
0.6529	Remote Similarity	NPD8080	Discontinued
0.6529	Remote Similarity	NPD5988	Approved
0.6522	Remote Similarity	NPD6617	Approved
0.6522	Remote Similarity	NPD6869	Approved
0.6522	Remote Similarity	NPD8130	Phase 1
0.6522	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6847	Approved
0.6504	Remote Similarity	NPD6336	Discontinued
0.6491	Remote Similarity	NPD6012	Approved
0.6491	Remote Similarity	NPD6014	Approved
0.6491	Remote Similarity	NPD6013	Approved
0.648	Remote Similarity	NPD7319	Approved
0.6476	Remote Similarity	NPD8034	Phase 2
0.6476	Remote Similarity	NPD8035	Phase 2
0.6465	Remote Similarity	NPD5369	Approved
0.6449	Remote Similarity	NPD5695	Phase 3
0.6446	Remote Similarity	NPD8515	Approved
0.6446	Remote Similarity	NPD8516	Approved
0.6446	Remote Similarity	NPD8517	Approved
0.6446	Remote Similarity	NPD8513	Phase 3
0.6435	Remote Similarity	NPD4634	Approved
0.6435	Remote Similarity	NPD6371	Approved
0.6422	Remote Similarity	NPD5696	Approved
0.64	Remote Similarity	NPD6435	Approved
0.64	Remote Similarity	NPD6033	Approved
0.6396	Remote Similarity	NPD8086	Approved
0.6396	Remote Similarity	NPD8084	Approved
0.6396	Remote Similarity	NPD8138	Approved
0.6396	Remote Similarity	NPD8083	Approved
0.6396	Remote Similarity	NPD8085	Approved
0.6396	Remote Similarity	NPD8139	Approved
0.6396	Remote Similarity	NPD8082	Approved
0.6389	Remote Similarity	NPD7839	Suspended
0.6385	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7507	Approved
0.6346	Remote Similarity	NPD6672	Approved
0.6346	Remote Similarity	NPD5737	Approved
0.6339	Remote Similarity	NPD8276	Approved
0.6339	Remote Similarity	NPD8275	Approved
0.6337	Remote Similarity	NPD6110	Phase 1
0.633	Remote Similarity	NPD7902	Approved
0.6311	Remote Similarity	NPD5786	Approved
0.6306	Remote Similarity	NPD1700	Approved
0.6283	Remote Similarity	NPD8081	Approved
0.6273	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6008	Approved
0.6228	Remote Similarity	NPD8393	Approved
0.6214	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7748	Approved
0.62	Remote Similarity	NPD5368	Approved
0.6198	Remote Similarity	NPD6335	Approved
0.619	Remote Similarity	NPD8074	Phase 3
0.6186	Remote Similarity	NPD6053	Discontinued
0.6183	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4755	Approved
0.6176	Remote Similarity	NPD3669	Approved
0.6176	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7515	Phase 2
0.6167	Remote Similarity	NPD6274	Approved
0.6162	Remote Similarity	NPD4802	Phase 2
0.6162	Remote Similarity	NPD4238	Approved
0.616	Remote Similarity	NPD8340	Approved
0.616	Remote Similarity	NPD8341	Approved
0.616	Remote Similarity	NPD8299	Approved
0.616	Remote Similarity	NPD8342	Approved
0.6154	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7909	Approved
0.6154	Remote Similarity	NPD6098	Approved
0.6148	Remote Similarity	NPD7100	Approved
0.6148	Remote Similarity	NPD7101	Approved
0.6147	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD1780	Approved
0.6139	Remote Similarity	NPD1779	Approved
0.6132	Remote Similarity	NPD6904	Approved
0.6132	Remote Similarity	NPD6673	Approved
0.6132	Remote Similarity	NPD6080	Approved
0.6126	Remote Similarity	NPD7638	Approved
0.6124	Remote Similarity	NPD7260	Phase 2
0.6116	Remote Similarity	NPD6317	Approved
0.6111	Remote Similarity	NPD8451	Approved
0.6107	Remote Similarity	NPD8415	Approved
0.61	Remote Similarity	NPD7329	Approved
0.6091	Remote Similarity	NPD4697	Phase 3
0.6078	Remote Similarity	NPD4270	Approved
0.6078	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4269	Approved
0.6075	Remote Similarity	NPD7838	Discovery
0.6071	Remote Similarity	NPD7639	Approved
0.6071	Remote Similarity	NPD5286	Approved
0.6071	Remote Similarity	NPD4700	Approved
0.6071	Remote Similarity	NPD4696	Approved
0.6071	Remote Similarity	NPD7640	Approved
0.6071	Remote Similarity	NPD5285	Approved
0.6066	Remote Similarity	NPD6314	Approved
0.6066	Remote Similarity	NPD7641	Discontinued
0.6066	Remote Similarity	NPD6313	Approved
0.6063	Remote Similarity	NPD8448	Approved
0.6055	Remote Similarity	NPD7900	Approved
0.6055	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6908	Approved
0.6048	Remote Similarity	NPD6909	Approved
0.6048	Remote Similarity	NPD8269	Approved
0.6048	Remote Similarity	NPD8267	Approved
0.6048	Remote Similarity	NPD8268	Approved
0.6048	Remote Similarity	NPD8266	Approved
0.6033	Remote Similarity	NPD6868	Approved
0.6019	Remote Similarity	NPD6050	Approved
0.6019	Remote Similarity	NPD7637	Suspended
0.6019	Remote Similarity	NPD4788	Approved
0.6018	Remote Similarity	NPD5344	Discontinued
0.6018	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD6422	Discontinued
0.5981	Remote Similarity	NPD5328	Approved
0.5981	Remote Similarity	NPD4753	Phase 2
0.5965	Remote Similarity	NPD8301	Approved
0.5965	Remote Similarity	NPD5225	Approved
0.5965	Remote Similarity	NPD5211	Phase 2
0.5965	Remote Similarity	NPD4633	Approved
0.5965	Remote Similarity	NPD8300	Approved
0.5965	Remote Similarity	NPD5226	Approved
0.5965	Remote Similarity	NPD5224	Approved
0.5962	Remote Similarity	NPD4786	Approved
0.5957	Remote Similarity	NPD898	Approved
0.5957	Remote Similarity	NPD897	Approved
0.5957	Remote Similarity	NPD896	Approved
0.5954	Remote Similarity	NPD6845	Suspended
0.5952	Remote Similarity	NPD7642	Approved
0.5948	Remote Similarity	NPD4768	Approved
0.5948	Remote Similarity	NPD4767	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