NPASS Compound

Structure

NPC469798 OpenBabel07101718202D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1945 1.8838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8344 3.5780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 4 13 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 18 2 0 0 0 0 12 7 1 1 0 0 0 12 14 1 0 0 0 0 13 20 2 0 0 0 0 14 5 1 6 0 0 0 14 15 1 0 0 0 0 15 19 1 6 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 19 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.17
Volume:	333.489
LogP:	2.694
LogD:	1.825
LogS:	-2.953
# Rotatable Bonds:	2
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.793
Synthetic Accessibility Score:	4.285
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.111
MDCK Permeability:	2.374609721300658e-05
Pgp-inhibitor:	0.157
Pgp-substrate:	0.069
Human Intestinal Absorption (HIA):	0.05
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.738
Plasma Protein Binding (PPB):	84.85204315185547%
Volume Distribution (VD):	0.315
Pgp-substrate:	12.660577774047852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.732
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.139
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.35
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	4.746
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.423
Drug-inuced Liver Injury (DILI):	0.204
AMES Toxicity:	0.41
Rat Oral Acute Toxicity:	0.323
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.946
Carcinogencity:	0.694
Eye Corrosion:	0.083
Eye Irritation:	0.209
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC469798

Natural Product ID:	NPC469798
*Common Name:**	Globostelletin F
IUPAC Name:	(E,4Z)-4-[(3aS,5aS,9aS,9bS)-3a-methyl-2,7-dioxo-4,5,5a,6,8,9,9a,9b-octahydro-1H-cyclopenta[a]naphthalen-3-ylidene]pent-2-enoic acid
Synonyms:	Globostelletin F
Standard InCHIKey:	GAHQYTUGPPZEML-GVACEKNUSA-N
Standard InCHI:	InChI=1S/C19H24O4/c1-11(3-6-17(22)23)18-16(21)10-15-14-5-4-13(20)9-12(14)7-8-19(15,18)2/h3,6,12,14-15H,4-5,7-10H2,1-2H3,(H,22,23)/b6-3+,18-11+/t12-,14-,15-,19-/m0/s1
SMILES:	O=C1CC[C@H]2[C@H](C1)CC[C@]1([C@H]2CC(=O)/C/1=C(C=CC(=O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173322
PubChem CID:	49799339
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids

*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
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	50000.0	nM	PMID[538459]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[538459]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000.0	nM	PMID[538459]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	50000.0	nM	PMID[538459]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[538459]

☑ 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 NPC469798 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	141
0.1-0.2	1112
0.2-0.3	6094
0.3-0.4	15442
0.4-0.5	9015
0.5-0.6	7371
0.6-0.7	2971
0.7-0.8	468
0.8-0.85	60
0.85-0.9	11
0.9-0.95	4
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469797
0.9737	High Similarity	NPC469804
0.9737	High Similarity	NPC469806
0.9737	High Similarity	NPC469805
0.9737	High Similarity	NPC469799
0.961	High Similarity	NPC279639
0.961	High Similarity	NPC3856
0.9067	High Similarity	NPC469803
0.8902	High Similarity	NPC476293
0.8875	High Similarity	NPC474790
0.8875	High Similarity	NPC474976
0.8816	High Similarity	NPC476346
0.8765	High Similarity	NPC87552
0.875	High Similarity	NPC472239
0.8706	High Similarity	NPC473986
0.8706	High Similarity	NPC474018
0.8684	High Similarity	NPC474796
0.8684	High Similarity	NPC474797
0.8684	High Similarity	NPC329866
0.8667	High Similarity	NPC133253
0.8667	High Similarity	NPC21944
0.8659	High Similarity	NPC60350
0.8553	High Similarity	NPC109576
0.8553	High Similarity	NPC56747
0.8553	High Similarity	NPC180015
0.8553	High Similarity	NPC130016
0.8537	High Similarity	NPC181743
0.8537	High Similarity	NPC178025
0.8537	High Similarity	NPC16287
0.8519	High Similarity	NPC3511
0.8519	High Similarity	NPC472867
0.8519	High Similarity	NPC142253
0.8452	Intermediate Similarity	NPC75315
0.8452	Intermediate Similarity	NPC163016
0.8434	Intermediate Similarity	NPC8571
0.8315	Intermediate Similarity	NPC301534
0.8315	Intermediate Similarity	NPC250757
0.8276	Intermediate Similarity	NPC204341
0.8256	Intermediate Similarity	NPC262043
0.8256	Intermediate Similarity	NPC474844
0.8235	Intermediate Similarity	NPC236618
0.8228	Intermediate Similarity	NPC469796
0.8228	Intermediate Similarity	NPC469793
0.8193	Intermediate Similarity	NPC97913
0.8182	Intermediate Similarity	NPC54123
0.814	Intermediate Similarity	NPC117122
0.8125	Intermediate Similarity	NPC91665
0.8118	Intermediate Similarity	NPC186975
0.8118	Intermediate Similarity	NPC472869
0.8095	Intermediate Similarity	NPC19849
0.8095	Intermediate Similarity	NPC164577
0.8095	Intermediate Similarity	NPC248758
0.8095	Intermediate Similarity	NPC472864
0.8072	Intermediate Similarity	NPC94200
0.8068	Intermediate Similarity	NPC23217
0.8052	Intermediate Similarity	NPC251929
0.8052	Intermediate Similarity	NPC2634
0.8052	Intermediate Similarity	NPC265782
0.8046	Intermediate Similarity	NPC66344
0.8025	Intermediate Similarity	NPC198240
0.8023	Intermediate Similarity	NPC136948
0.8	Intermediate Similarity	NPC269638
0.8	Intermediate Similarity	NPC19907
0.8	Intermediate Similarity	NPC29447
0.7978	Intermediate Similarity	NPC469939
0.7976	Intermediate Similarity	NPC118423
0.7975	Intermediate Similarity	NPC20025
0.7957	Intermediate Similarity	NPC282524
0.7949	Intermediate Similarity	NPC305501
0.7935	Intermediate Similarity	NPC57079
0.7935	Intermediate Similarity	NPC108368
0.7931	Intermediate Similarity	NPC72397
0.7931	Intermediate Similarity	NPC472870
0.7922	Intermediate Similarity	NPC139397
0.7907	Intermediate Similarity	NPC168248
0.7901	Intermediate Similarity	NPC61952
0.7889	Intermediate Similarity	NPC299100
0.7882	Intermediate Similarity	NPC472865
0.7875	Intermediate Similarity	NPC473171
0.7872	Intermediate Similarity	NPC320447
0.7857	Intermediate Similarity	NPC320514
0.7857	Intermediate Similarity	NPC268122
0.7849	Intermediate Similarity	NPC266955
0.7848	Intermediate Similarity	NPC474228
0.7848	Intermediate Similarity	NPC251705
0.7848	Intermediate Similarity	NPC303613
0.7841	Intermediate Similarity	NPC118011
0.7841	Intermediate Similarity	NPC36668
0.7821	Intermediate Similarity	NPC260040
0.7821	Intermediate Similarity	NPC307176
0.7816	Intermediate Similarity	NPC128644
0.7802	Intermediate Similarity	NPC171395
0.7802	Intermediate Similarity	NPC476174
0.7802	Intermediate Similarity	NPC180950
0.7789	Intermediate Similarity	NPC72151
0.7778	Intermediate Similarity	NPC69408
0.7778	Intermediate Similarity	NPC180886
0.7778	Intermediate Similarity	NPC242069
0.7766	Intermediate Similarity	NPC115899
0.7765	Intermediate Similarity	NPC49019
0.7763	Intermediate Similarity	NPC255781
0.7753	Intermediate Similarity	NPC474842
0.7753	Intermediate Similarity	NPC472866
0.7753	Intermediate Similarity	NPC475965
0.775	Intermediate Similarity	NPC255021
0.775	Intermediate Similarity	NPC309852
0.7742	Intermediate Similarity	NPC166745
0.7742	Intermediate Similarity	NPC235464
0.7738	Intermediate Similarity	NPC4166
0.7738	Intermediate Similarity	NPC477372
0.7738	Intermediate Similarity	NPC278459
0.7727	Intermediate Similarity	NPC48107
0.7722	Intermediate Similarity	NPC5701
0.7722	Intermediate Similarity	NPC115023
0.7722	Intermediate Similarity	NPC234707
0.7722	Intermediate Similarity	NPC470078
0.7717	Intermediate Similarity	NPC29152
0.7711	Intermediate Similarity	NPC190211
0.7701	Intermediate Similarity	NPC6247
0.7692	Intermediate Similarity	NPC474690
0.7683	Intermediate Similarity	NPC97377
0.7667	Intermediate Similarity	NPC470113
0.7654	Intermediate Similarity	NPC65650
0.7654	Intermediate Similarity	NPC255650
0.7654	Intermediate Similarity	NPC293803
0.7647	Intermediate Similarity	NPC311092
0.7647	Intermediate Similarity	NPC100297
0.7634	Intermediate Similarity	NPC156546
0.7634	Intermediate Similarity	NPC2049
0.7632	Intermediate Similarity	NPC107258
0.7625	Intermediate Similarity	NPC470044
0.7625	Intermediate Similarity	NPC470045
0.7614	Intermediate Similarity	NPC476409
0.7614	Intermediate Similarity	NPC477228
0.7614	Intermediate Similarity	NPC181327
0.7609	Intermediate Similarity	NPC88310
0.7609	Intermediate Similarity	NPC293052
0.7609	Intermediate Similarity	NPC209355
0.7604	Intermediate Similarity	NPC475050
0.7604	Intermediate Similarity	NPC475526
0.7604	Intermediate Similarity	NPC473283
0.7604	Intermediate Similarity	NPC329345
0.7595	Intermediate Similarity	NPC282593
0.7595	Intermediate Similarity	NPC35734
0.7595	Intermediate Similarity	NPC159577
0.759	Intermediate Similarity	NPC169095
0.759	Intermediate Similarity	NPC74410
0.759	Intermediate Similarity	NPC105197
0.7586	Intermediate Similarity	NPC472940
0.7586	Intermediate Similarity	NPC142649
0.7586	Intermediate Similarity	NPC11711
0.7586	Intermediate Similarity	NPC472931
0.7582	Intermediate Similarity	NPC472871
0.7579	Intermediate Similarity	NPC99411
0.7564	Intermediate Similarity	NPC188292
0.7564	Intermediate Similarity	NPC310992
0.7564	Intermediate Similarity	NPC260474
0.7561	Intermediate Similarity	NPC474463
0.7558	Intermediate Similarity	NPC168188
0.7558	Intermediate Similarity	NPC310470
0.7558	Intermediate Similarity	NPC470015
0.7558	Intermediate Similarity	NPC105803
0.7558	Intermediate Similarity	NPC83569
0.7558	Intermediate Similarity	NPC69279
0.7558	Intermediate Similarity	NPC102197
0.7558	Intermediate Similarity	NPC41539
0.7532	Intermediate Similarity	NPC81907
0.7532	Intermediate Similarity	NPC323005
0.7532	Intermediate Similarity	NPC259156
0.7532	Intermediate Similarity	NPC242945
0.7531	Intermediate Similarity	NPC3753
0.7531	Intermediate Similarity	NPC237591
0.7529	Intermediate Similarity	NPC147066
0.7529	Intermediate Similarity	NPC90055
0.7528	Intermediate Similarity	NPC196407
0.7527	Intermediate Similarity	NPC456
0.7527	Intermediate Similarity	NPC471153
0.7527	Intermediate Similarity	NPC472941
0.75	Intermediate Similarity	NPC155332
0.75	Intermediate Similarity	NPC472863
0.75	Intermediate Similarity	NPC114540
0.75	Intermediate Similarity	NPC477371
0.75	Intermediate Similarity	NPC181204
0.75	Intermediate Similarity	NPC212210
0.75	Intermediate Similarity	NPC170793
0.75	Intermediate Similarity	NPC32577
0.7474	Intermediate Similarity	NPC35751
0.7473	Intermediate Similarity	NPC476187
0.747	Intermediate Similarity	NPC165711
0.7468	Intermediate Similarity	NPC182815
0.7468	Intermediate Similarity	NPC256846
0.7449	Intermediate Similarity	NPC189863
0.7449	Intermediate Similarity	NPC266570
0.7447	Intermediate Similarity	NPC208094
0.7447	Intermediate Similarity	NPC474938
0.7447	Intermediate Similarity	NPC253826
0.7447	Intermediate Similarity	NPC110937
0.7447	Intermediate Similarity	NPC474785
0.7444	Intermediate Similarity	NPC5509
0.7444	Intermediate Similarity	NPC285982

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 NPC469798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	1289
0.2-0.3	4184
0.3-0.4	2527
0.4-0.5	568
0.5-0.6	222
0.6-0.7	173
0.7-0.8	51
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
0.8442	Intermediate Similarity	NPD4058	Approved
0.8052	Intermediate Similarity	NPD4691	Approved
0.7975	Intermediate Similarity	NPD4687	Approved
0.7922	Intermediate Similarity	NPD4137	Phase 3
0.7821	Intermediate Similarity	NPD4747	Approved
0.775	Intermediate Similarity	NPD5733	Approved
0.7722	Intermediate Similarity	NPD5276	Approved
0.7667	Intermediate Similarity	NPD5284	Approved
0.7667	Intermediate Similarity	NPD5281	Approved
0.7356	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4623	Approved
0.7303	Intermediate Similarity	NPD4519	Discontinued
0.7303	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5694	Approved
0.7253	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4221	Approved
0.7241	Intermediate Similarity	NPD4223	Phase 3
0.7237	Intermediate Similarity	NPD4192	Approved
0.7237	Intermediate Similarity	NPD4191	Approved
0.7237	Intermediate Similarity	NPD4193	Approved
0.7237	Intermediate Similarity	NPD4194	Approved
0.7176	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3617	Approved
0.7174	Intermediate Similarity	NPD5207	Approved
0.7174	Intermediate Similarity	NPD5692	Phase 3
0.7143	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7113	Intermediate Similarity	NPD6404	Discontinued
0.7111	Intermediate Similarity	NPD7146	Approved
0.7111	Intermediate Similarity	NPD6684	Approved
0.7111	Intermediate Similarity	NPD4694	Approved
0.7111	Intermediate Similarity	NPD7521	Approved
0.7111	Intermediate Similarity	NPD5280	Approved
0.7111	Intermediate Similarity	NPD7334	Approved
0.7111	Intermediate Similarity	NPD5690	Phase 2
0.7111	Intermediate Similarity	NPD6409	Approved
0.7111	Intermediate Similarity	NPD5330	Approved
0.7097	Intermediate Similarity	NPD5693	Phase 1
0.7097	Intermediate Similarity	NPD6050	Approved
0.7079	Intermediate Similarity	NPD4197	Approved
0.7079	Intermediate Similarity	NPD3665	Phase 1
0.7079	Intermediate Similarity	NPD3666	Approved
0.7079	Intermediate Similarity	NPD3133	Approved
0.7065	Intermediate Similarity	NPD6080	Approved
0.7065	Intermediate Similarity	NPD6673	Approved
0.7065	Intermediate Similarity	NPD6904	Approved
0.7011	Intermediate Similarity	NPD4695	Discontinued
0.7	Intermediate Similarity	NPD5329	Approved
0.6957	Remote Similarity	NPD5208	Approved
0.6957	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD4688	Approved
0.6923	Remote Similarity	NPD3618	Phase 1
0.6923	Remote Similarity	NPD4689	Approved
0.6923	Remote Similarity	NPD5279	Phase 3
0.6923	Remote Similarity	NPD4138	Approved
0.6923	Remote Similarity	NPD4693	Phase 3
0.6923	Remote Similarity	NPD4690	Approved
0.6923	Remote Similarity	NPD5205	Approved
0.6915	Remote Similarity	NPD7637	Suspended
0.6915	Remote Similarity	NPD6079	Approved
0.6907	Remote Similarity	NPD6084	Phase 2
0.6907	Remote Similarity	NPD6083	Phase 2
0.6897	Remote Similarity	NPD4195	Approved
0.6882	Remote Similarity	NPD4753	Phase 2
0.6875	Remote Similarity	NPD5210	Approved
0.6875	Remote Similarity	NPD4629	Approved
0.6875	Remote Similarity	NPD5695	Phase 3
0.6875	Remote Similarity	NPD5654	Approved
0.6854	Remote Similarity	NPD3667	Approved
0.6848	Remote Similarity	NPD3573	Approved
0.6842	Remote Similarity	NPD6399	Phase 3
0.6837	Remote Similarity	NPD5696	Approved
0.6813	Remote Similarity	NPD5363	Approved
0.6813	Remote Similarity	NPD1694	Approved
0.6809	Remote Similarity	NPD5785	Approved
0.6804	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5222	Approved
0.6804	Remote Similarity	NPD5221	Approved
0.68	Remote Similarity	NPD5211	Phase 2
0.6768	Remote Similarity	NPD7640	Approved
0.6768	Remote Similarity	NPD7639	Approved
0.6739	Remote Similarity	NPD6098	Approved
0.6737	Remote Similarity	NPD7515	Phase 2
0.6735	Remote Similarity	NPD5173	Approved
0.6735	Remote Similarity	NPD5959	Approved
0.6703	Remote Similarity	NPD4786	Approved
0.6703	Remote Similarity	NPD3668	Phase 3
0.6702	Remote Similarity	NPD5328	Approved
0.6701	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD5133	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6635	Remote Similarity	NPD6881	Approved
0.6635	Remote Similarity	NPD6011	Approved
0.6635	Remote Similarity	NPD6899	Approved
0.6633	Remote Similarity	NPD7614	Phase 1
0.6632	Remote Similarity	NPD4096	Approved
0.6606	Remote Similarity	NPD7115	Discovery
0.66	Remote Similarity	NPD5285	Approved
0.66	Remote Similarity	NPD4696	Approved
0.66	Remote Similarity	NPD5286	Approved
0.6598	Remote Similarity	NPD6001	Approved
0.6598	Remote Similarity	NPD7748	Approved
0.6598	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4518	Approved
0.6571	Remote Similarity	NPD6012	Approved
0.6571	Remote Similarity	NPD6014	Approved
0.6571	Remote Similarity	NPD6013	Approved
0.6556	Remote Similarity	NPD8028	Phase 2
0.6535	Remote Similarity	NPD5223	Approved
0.6509	Remote Similarity	NPD7102	Approved
0.6509	Remote Similarity	NPD7290	Approved
0.6509	Remote Similarity	NPD6883	Approved
0.6495	Remote Similarity	NPD4202	Approved
0.6484	Remote Similarity	NPD5209	Approved
0.6484	Remote Similarity	NPD4270	Approved
0.6484	Remote Similarity	NPD4269	Approved
0.6471	Remote Similarity	NPD5091	Approved
0.6471	Remote Similarity	NPD5225	Approved
0.6471	Remote Similarity	NPD4633	Approved
0.6471	Remote Similarity	NPD5226	Approved
0.6471	Remote Similarity	NPD5224	Approved
0.6465	Remote Similarity	NPD4697	Phase 3
0.6452	Remote Similarity	NPD1696	Phase 3
0.6449	Remote Similarity	NPD6847	Approved
0.6449	Remote Similarity	NPD6649	Approved
0.6449	Remote Similarity	NPD6869	Approved
0.6449	Remote Similarity	NPD8130	Phase 1
0.6449	Remote Similarity	NPD6650	Approved
0.6449	Remote Similarity	NPD6617	Approved
0.6444	Remote Similarity	NPD4252	Approved
0.6442	Remote Similarity	NPD6675	Approved
0.6442	Remote Similarity	NPD6402	Approved
0.6442	Remote Similarity	NPD7128	Approved
0.6442	Remote Similarity	NPD5739	Approved
0.6413	Remote Similarity	NPD5362	Discontinued
0.6413	Remote Similarity	NPD4788	Approved
0.641	Remote Similarity	NPD287	Approved
0.6408	Remote Similarity	NPD5175	Approved
0.6408	Remote Similarity	NPD5174	Approved
0.64	Remote Similarity	NPD7902	Approved
0.64	Remote Similarity	NPD4755	Approved
0.6389	Remote Similarity	NPD6882	Approved
0.6389	Remote Similarity	NPD8297	Approved
0.6381	Remote Similarity	NPD5701	Approved
0.6381	Remote Similarity	NPD6614	Approved
0.6374	Remote Similarity	NPD4692	Approved
0.6374	Remote Similarity	NPD4139	Approved
0.6337	Remote Similarity	NPD4225	Approved
0.633	Remote Similarity	NPD4632	Approved
0.6321	Remote Similarity	NPD7320	Approved
0.6311	Remote Similarity	NPD7632	Discontinued
0.63	Remote Similarity	NPD7732	Phase 3
0.6292	Remote Similarity	NPD4756	Discovery
0.6279	Remote Similarity	NPD6081	Approved
0.6277	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4700	Approved
0.6265	Remote Similarity	NPD4224	Phase 2
0.6264	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7514	Phase 3
0.6263	Remote Similarity	NPD7900	Approved
0.6263	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6373	Approved
0.6262	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD6052	Approved
0.6222	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7145	Approved
0.6216	Remote Similarity	NPD6868	Approved
0.6211	Remote Similarity	NPD5786	Approved
0.62	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6049	Phase 2
0.6196	Remote Similarity	NPD6902	Approved
0.6168	Remote Similarity	NPD4730	Approved
0.6168	Remote Similarity	NPD5168	Approved
0.6168	Remote Similarity	NPD4729	Approved
0.6168	Remote Similarity	NPD6686	Approved
0.6163	Remote Similarity	NPD7144	Approved
0.6163	Remote Similarity	NPD7143	Approved
0.6162	Remote Similarity	NPD5778	Approved
0.6162	Remote Similarity	NPD5779	Approved
0.6161	Remote Similarity	NPD6317	Approved
0.6161	Remote Similarity	NPD6009	Approved
0.6147	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6008	Approved
0.6117	Remote Similarity	NPD2066	Phase 3
0.6111	Remote Similarity	NPD6925	Approved
0.6111	Remote Similarity	NPD5776	Phase 2
0.6106	Remote Similarity	NPD6314	Approved
0.6106	Remote Similarity	NPD6335	Approved
0.6106	Remote Similarity	NPD6313	Approved
0.61	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4754	Approved
0.6092	Remote Similarity	NPD7151	Approved
0.6092	Remote Similarity	NPD7152	Approved
0.6092	Remote Similarity	NPD7150	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