NPASS Compound

Structure

NPC474463 OpenBabel07101719522D 30 33 0 0 1 0 0 0 0 0999 V2000 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 4.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4251 7.3074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8289 5.1974 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1379 6.1485 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 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4688 6.8916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1161 6.3564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 5 30 1 0 0 0 0 6 7 2 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 1 1 1 0 0 0 17 22 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 28 2 0 0 0 0 21 9 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 24 26 1 1 0 0 0 25 29 2 0 0 0 0 25 30 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.28
Volume:	454.511
LogP:	6.348
LogD:	5.427
LogS:	-5.372
# Rotatable Bonds:	5
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	4.591
Fsp3:	0.704
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.664
MDCK Permeability:	3.282385296188295e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.767
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	91.94281768798828%
Volume Distribution (VD):	1.113
Pgp-substrate:	3.184478998184204%

ADMET: Metabolism

CYP1A2-inhibitor:	0.623
CYP1A2-substrate:	0.4
CYP2C19-inhibitor:	0.92
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.91
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.83
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.97
CYP3A4-substrate:	0.778

ADMET: Excretion

Clearance (CL):	10.353
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.16
Human Hepatotoxicity (H-HT):	0.639
Drug-inuced Liver Injury (DILI):	0.469
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.984
Carcinogencity:	0.625
Eye Corrosion:	0.899
Eye Irritation:	0.677
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC474463

Natural Product ID:	NPC474463
*Common Name:**	Methyl (22E)-3-Oxo-24-Norcholesta-1,4,22-Trien-26-Oate
IUPAC Name:	methyl (E,5R)-5-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-methylhex-3-enoate
Synonyms:
Standard InCHIKey:	SPYDBHQUKUZVQJ-MDNIRYJNSA-N
Standard InCHI:	InChI=1S/C27H38O3/c1-17(6-7-18(2)25(29)30-5)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h6-7,12,14,16-18,21-24H,8-11,13,15H2,1-5H3/b7-6+/t17-,18?,21+,22-,23+,24+,26+,27-/m1/s1
SMILES:	COC(=O)C(/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469417
PubChem CID:	11200718
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003569] Pregnane steroids [CHEMONTID:0001468] Gluco/mineralocorticoids, progestogins and derivatives

*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
NPO11876	Anthomastus bathyproctus	Species	Alcyoniidae	Eukaryota	n.a.	Antarctic	n.a.	PMID[16038562]
NPO11876	Anthomastus bathyproctus	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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	20200.0	nM	PMID[524210]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	21400.0	nM	PMID[524210]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	22400.0	nM	PMID[524210]

☑ 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 NPC474463 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	164
0.1-0.2	1479
0.2-0.3	9640
0.3-0.4	14264
0.4-0.5	7603
0.5-0.6	6480
0.6-0.7	2648
0.7-0.8	370
0.8-0.85	39
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9324	High Similarity	NPC190211
0.9189	High Similarity	NPC105197
0.8857	High Similarity	NPC176107
0.8714	High Similarity	NPC92327
0.8514	High Similarity	NPC303613
0.8514	High Similarity	NPC474228
0.8514	High Similarity	NPC251705
0.8481	Intermediate Similarity	NPC100297
0.8434	Intermediate Similarity	NPC177141
0.8421	Intermediate Similarity	NPC69408
0.84	Intermediate Similarity	NPC309852
0.8378	Intermediate Similarity	NPC234707
0.8378	Intermediate Similarity	NPC54123
0.8378	Intermediate Similarity	NPC305501
0.8378	Intermediate Similarity	NPC115023
0.8333	Intermediate Similarity	NPC273199
0.8289	Intermediate Similarity	NPC293803
0.8267	Intermediate Similarity	NPC470045
0.8267	Intermediate Similarity	NPC470044
0.825	Intermediate Similarity	NPC327969
0.825	Intermediate Similarity	NPC321289
0.825	Intermediate Similarity	NPC472239
0.8243	Intermediate Similarity	NPC35734
0.8243	Intermediate Similarity	NPC282593
0.8243	Intermediate Similarity	NPC307176
0.8243	Intermediate Similarity	NPC2634
0.8243	Intermediate Similarity	NPC265782
0.8243	Intermediate Similarity	NPC251929
0.8243	Intermediate Similarity	NPC159577
0.8228	Intermediate Similarity	NPC474509
0.8194	Intermediate Similarity	NPC176171
0.8171	Intermediate Similarity	NPC29447
0.8158	Intermediate Similarity	NPC255021
0.8148	Intermediate Similarity	NPC474976
0.8148	Intermediate Similarity	NPC474790
0.8108	Intermediate Similarity	NPC182815
0.8108	Intermediate Similarity	NPC139397
0.8101	Intermediate Similarity	NPC44083
0.8101	Intermediate Similarity	NPC153987
0.8052	Intermediate Similarity	NPC255650
0.8049	Intermediate Similarity	NPC320801
0.8049	Intermediate Similarity	NPC33913
0.8025	Intermediate Similarity	NPC3511
0.8025	Intermediate Similarity	NPC142253
0.8025	Intermediate Similarity	NPC472867
0.8025	Intermediate Similarity	NPC320514
0.8023	Intermediate Similarity	NPC218301
0.8	Intermediate Similarity	NPC260040
0.8	Intermediate Similarity	NPC474844
0.7975	Intermediate Similarity	NPC470052
0.7973	Intermediate Similarity	NPC20610
0.7955	Intermediate Similarity	NPC281134
0.7922	Intermediate Similarity	NPC329866
0.7922	Intermediate Similarity	NPC474796
0.7922	Intermediate Similarity	NPC474797
0.7895	Intermediate Similarity	NPC470078
0.7875	Intermediate Similarity	NPC90965
0.7875	Intermediate Similarity	NPC170793
0.7857	Intermediate Similarity	NPC264127
0.7857	Intermediate Similarity	NPC195640
0.7848	Intermediate Similarity	NPC472300
0.7831	Intermediate Similarity	NPC178025
0.7831	Intermediate Similarity	NPC472265
0.7831	Intermediate Similarity	NPC87552
0.7831	Intermediate Similarity	NPC181743
0.7831	Intermediate Similarity	NPC16287
0.7821	Intermediate Similarity	NPC65650
0.7821	Intermediate Similarity	NPC473171
0.7805	Intermediate Similarity	NPC469805
0.7805	Intermediate Similarity	NPC469804
0.7792	Intermediate Similarity	NPC144947
0.7791	Intermediate Similarity	NPC146554
0.7791	Intermediate Similarity	NPC262043
0.7765	Intermediate Similarity	NPC476293
0.7765	Intermediate Similarity	NPC75315
0.7765	Intermediate Similarity	NPC163016
0.7763	Intermediate Similarity	NPC40574
0.775	Intermediate Similarity	NPC469996
0.775	Intermediate Similarity	NPC82635
0.7738	Intermediate Similarity	NPC60350
0.7738	Intermediate Similarity	NPC8571
0.7738	Intermediate Similarity	NPC323765
0.7738	Intermediate Similarity	NPC470223
0.7733	Intermediate Similarity	NPC188292
0.7733	Intermediate Similarity	NPC260474
0.7722	Intermediate Similarity	NPC4509
0.7722	Intermediate Similarity	NPC469793
0.7722	Intermediate Similarity	NPC469796
0.7714	Intermediate Similarity	NPC60772
0.7711	Intermediate Similarity	NPC470015
0.7711	Intermediate Similarity	NPC279639
0.7711	Intermediate Similarity	NPC118423
0.7711	Intermediate Similarity	NPC168188
0.7711	Intermediate Similarity	NPC3856
0.7703	Intermediate Similarity	NPC323005
0.7703	Intermediate Similarity	NPC185587
0.7692	Intermediate Similarity	NPC20025
0.7683	Intermediate Similarity	NPC477372
0.7683	Intermediate Similarity	NPC147066
0.7683	Intermediate Similarity	NPC475833
0.7674	Intermediate Similarity	NPC97884
0.7674	Intermediate Similarity	NPC472220
0.7667	Intermediate Similarity	NPC111684
0.7667	Intermediate Similarity	NPC58052
0.7662	Intermediate Similarity	NPC5701
0.7647	Intermediate Similarity	NPC472863
0.764	Intermediate Similarity	NPC128488
0.764	Intermediate Similarity	NPC304968
0.7632	Intermediate Similarity	NPC256846
0.7625	Intermediate Similarity	NPC470557
0.7595	Intermediate Similarity	NPC476346
0.759	Intermediate Similarity	NPC94200
0.759	Intermediate Similarity	NPC268122
0.759	Intermediate Similarity	NPC469806
0.759	Intermediate Similarity	NPC469799
0.759	Intermediate Similarity	NPC260956
0.759	Intermediate Similarity	NPC240302
0.7586	Intermediate Similarity	NPC305039
0.7586	Intermediate Similarity	NPC262858
0.7586	Intermediate Similarity	NPC472240
0.7582	Intermediate Similarity	NPC108078
0.7561	Intermediate Similarity	NPC469798
0.7561	Intermediate Similarity	NPC469797
0.7558	Intermediate Similarity	NPC136948
0.7558	Intermediate Similarity	NPC58063
0.7558	Intermediate Similarity	NPC93778
0.7556	Intermediate Similarity	NPC33473
0.7532	Intermediate Similarity	NPC477856
0.7532	Intermediate Similarity	NPC214770
0.7529	Intermediate Similarity	NPC311702
0.7529	Intermediate Similarity	NPC469948
0.7529	Intermediate Similarity	NPC123319
0.7529	Intermediate Similarity	NPC94531
0.7529	Intermediate Similarity	NPC11711
0.7528	Intermediate Similarity	NPC38232
0.7528	Intermediate Similarity	NPC79117
0.7527	Intermediate Similarity	NPC310981
0.75	Intermediate Similarity	NPC474842
0.75	Intermediate Similarity	NPC87141
0.75	Intermediate Similarity	NPC271784
0.75	Intermediate Similarity	NPC469561
0.75	Intermediate Similarity	NPC475965
0.7471	Intermediate Similarity	NPC28227
0.747	Intermediate Similarity	NPC38350
0.747	Intermediate Similarity	NPC201912
0.747	Intermediate Similarity	NPC278459
0.747	Intermediate Similarity	NPC6434
0.7468	Intermediate Similarity	NPC166797
0.7467	Intermediate Similarity	NPC242945
0.7467	Intermediate Similarity	NPC259156
0.7447	Intermediate Similarity	NPC271266
0.7447	Intermediate Similarity	NPC308351
0.7444	Intermediate Similarity	NPC294266
0.7442	Intermediate Similarity	NPC474732
0.7442	Intermediate Similarity	NPC31564
0.7442	Intermediate Similarity	NPC474778
0.7442	Intermediate Similarity	NPC475022
0.7442	Intermediate Similarity	NPC474970
0.7442	Intermediate Similarity	NPC222613
0.7442	Intermediate Similarity	NPC155011
0.7442	Intermediate Similarity	NPC474733
0.7442	Intermediate Similarity	NPC118648
0.7442	Intermediate Similarity	NPC168248
0.7442	Intermediate Similarity	NPC145879
0.7439	Intermediate Similarity	NPC471475
0.7439	Intermediate Similarity	NPC477371
0.7436	Intermediate Similarity	NPC225467
0.7436	Intermediate Similarity	NPC223187
0.7436	Intermediate Similarity	NPC181204
0.7436	Intermediate Similarity	NPC190035
0.7432	Intermediate Similarity	NPC212210
0.7432	Intermediate Similarity	NPC469662
0.7416	Intermediate Similarity	NPC473986
0.7416	Intermediate Similarity	NPC474018
0.7416	Intermediate Similarity	NPC23217
0.7416	Intermediate Similarity	NPC204341
0.7412	Intermediate Similarity	NPC214043
0.7412	Intermediate Similarity	NPC85774
0.7407	Intermediate Similarity	NPC91665
0.7403	Intermediate Similarity	NPC477857
0.7391	Intermediate Similarity	NPC292133
0.7386	Intermediate Similarity	NPC285982
0.7386	Intermediate Similarity	NPC474570
0.7386	Intermediate Similarity	NPC66344
0.7381	Intermediate Similarity	NPC142683
0.7363	Intermediate Similarity	NPC171395
0.7356	Intermediate Similarity	NPC475740
0.7356	Intermediate Similarity	NPC96496
0.7356	Intermediate Similarity	NPC128644
0.7349	Intermediate Similarity	NPC472478
0.7349	Intermediate Similarity	NPC267517
0.7342	Intermediate Similarity	NPC56747
0.7342	Intermediate Similarity	NPC276336
0.7342	Intermediate Similarity	NPC109576
0.7342	Intermediate Similarity	NPC130016
0.7342	Intermediate Similarity	NPC180015
0.7333	Intermediate Similarity	NPC251118
0.7333	Intermediate Similarity	NPC474736
0.7333	Intermediate Similarity	NPC107258
0.7333	Intermediate Similarity	NPC470923

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 NPC474463 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1541
0.2-0.3	4826
0.3-0.4	1884
0.4-0.5	385
0.5-0.6	148
0.6-0.7	161
0.7-0.8	56
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8243	Intermediate Similarity	NPD4747	Approved
0.8243	Intermediate Similarity	NPD4691	Approved
0.8158	Intermediate Similarity	NPD4058	Approved
0.8108	Intermediate Similarity	NPD4137	Phase 3
0.7922	Intermediate Similarity	NPD5733	Approved
0.7922	Intermediate Similarity	NPD4687	Approved
0.7882	Intermediate Similarity	NPD6672	Approved
0.7882	Intermediate Similarity	NPD5737	Approved
0.7857	Intermediate Similarity	NPD6409	Approved
0.7857	Intermediate Similarity	NPD5330	Approved
0.7857	Intermediate Similarity	NPD7146	Approved
0.7857	Intermediate Similarity	NPD6684	Approved
0.7857	Intermediate Similarity	NPD7521	Approved
0.7857	Intermediate Similarity	NPD7334	Approved
0.7674	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6903	Approved
0.7662	Intermediate Similarity	NPD5276	Approved
0.7654	Intermediate Similarity	NPD4195	Approved
0.7586	Intermediate Similarity	NPD6080	Approved
0.7586	Intermediate Similarity	NPD6673	Approved
0.7586	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5208	Approved
0.7442	Intermediate Similarity	NPD6098	Approved
0.7363	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6399	Phase 3
0.7303	Intermediate Similarity	NPD5207	Approved
0.7222	Intermediate Similarity	NPD5694	Approved
0.7222	Intermediate Similarity	NPD6079	Approved
0.7222	Intermediate Similarity	NPD6050	Approved
0.7222	Intermediate Similarity	NPD5693	Phase 1
0.7209	Intermediate Similarity	NPD4786	Approved
0.7204	Intermediate Similarity	NPD6084	Phase 2
0.7204	Intermediate Similarity	NPD6083	Phase 2
0.7176	Intermediate Similarity	NPD4221	Approved
0.7176	Intermediate Similarity	NPD4223	Phase 3
0.7159	Intermediate Similarity	NPD3573	Approved
0.7126	Intermediate Similarity	NPD5329	Approved
0.7111	Intermediate Similarity	NPD5692	Phase 3
0.7093	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6001	Approved
0.7045	Intermediate Similarity	NPD5690	Phase 2
0.7037	Intermediate Similarity	NPD4784	Approved
0.7037	Intermediate Similarity	NPD4785	Approved
0.7033	Intermediate Similarity	NPD5284	Approved
0.7033	Intermediate Similarity	NPD5281	Approved
0.7011	Intermediate Similarity	NPD4197	Approved
0.7011	Intermediate Similarity	NPD3133	Approved
0.7011	Intermediate Similarity	NPD3665	Phase 1
0.7011	Intermediate Similarity	NPD3666	Approved
0.7	Intermediate Similarity	NPD6051	Approved
0.7	Intermediate Similarity	NPD5328	Approved
0.6989	Remote Similarity	NPD5695	Phase 3
0.6977	Remote Similarity	NPD3667	Approved
0.6951	Remote Similarity	NPD6942	Approved
0.6951	Remote Similarity	NPD7339	Approved
0.6947	Remote Similarity	NPD5696	Approved
0.69	Remote Similarity	NPD6881	Approved
0.69	Remote Similarity	NPD6899	Approved
0.6854	Remote Similarity	NPD4690	Approved
0.6854	Remote Similarity	NPD5205	Approved
0.6854	Remote Similarity	NPD4688	Approved
0.6854	Remote Similarity	NPD4689	Approved
0.6854	Remote Similarity	NPD4138	Approved
0.6854	Remote Similarity	NPD4693	Phase 3
0.6854	Remote Similarity	NPD3618	Phase 1
0.6818	Remote Similarity	NPD3668	Phase 3
0.6813	Remote Similarity	NPD4753	Phase 2
0.6809	Remote Similarity	NPD5210	Approved
0.6809	Remote Similarity	NPD4629	Approved
0.68	Remote Similarity	NPD6614	Approved
0.68	Remote Similarity	NPD5697	Approved
0.679	Remote Similarity	NPD4243	Approved
0.6782	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7290	Approved
0.6765	Remote Similarity	NPD6883	Approved
0.6765	Remote Similarity	NPD7102	Approved
0.6744	Remote Similarity	NPD4695	Discontinued
0.6737	Remote Similarity	NPD5222	Approved
0.6737	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5221	Approved
0.6733	Remote Similarity	NPD6011	Approved
0.6706	Remote Similarity	NPD3617	Approved
0.6702	Remote Similarity	NPD7748	Approved
0.6702	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7900	Approved
0.67	Remote Similarity	NPD6008	Approved
0.67	Remote Similarity	NPD5739	Approved
0.67	Remote Similarity	NPD6402	Approved
0.67	Remote Similarity	NPD7128	Approved
0.67	Remote Similarity	NPD6675	Approved
0.6699	Remote Similarity	NPD6847	Approved
0.6699	Remote Similarity	NPD6649	Approved
0.6699	Remote Similarity	NPD6650	Approved
0.6699	Remote Similarity	NPD6617	Approved
0.6699	Remote Similarity	NPD6869	Approved
0.6699	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD8028	Phase 2
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6635	Remote Similarity	NPD6882	Approved
0.6635	Remote Similarity	NPD8297	Approved
0.6632	Remote Similarity	NPD5654	Approved
0.663	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7638	Approved
0.6596	Remote Similarity	NPD4202	Approved
0.6585	Remote Similarity	NPD7150	Approved
0.6585	Remote Similarity	NPD7152	Approved
0.6585	Remote Similarity	NPD7151	Approved
0.6569	Remote Similarity	NPD7320	Approved
0.6562	Remote Similarity	NPD7732	Phase 3
0.6556	Remote Similarity	NPD1694	Approved
0.6543	Remote Similarity	NPD6923	Approved
0.6543	Remote Similarity	NPD6922	Approved
0.6542	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD287	Approved
0.6531	Remote Similarity	NPD4696	Approved
0.6531	Remote Similarity	NPD7639	Approved
0.6531	Remote Similarity	NPD7640	Approved
0.6531	Remote Similarity	NPD5285	Approved
0.6531	Remote Similarity	NPD5286	Approved
0.6517	Remote Similarity	NPD4788	Approved
0.6505	Remote Similarity	NPD6372	Approved
0.6505	Remote Similarity	NPD6373	Approved
0.6495	Remote Similarity	NPD7902	Approved
0.6495	Remote Similarity	NPD5959	Approved
0.6494	Remote Similarity	NPD4191	Approved
0.6494	Remote Similarity	NPD4194	Approved
0.6494	Remote Similarity	NPD4192	Approved
0.6494	Remote Similarity	NPD4193	Approved
0.6484	Remote Similarity	NPD4519	Discontinued
0.6484	Remote Similarity	NPD4623	Approved
0.6471	Remote Similarity	NPD5701	Approved
0.6465	Remote Similarity	NPD5223	Approved
0.6449	Remote Similarity	NPD6868	Approved
0.6429	Remote Similarity	NPD6926	Approved
0.6429	Remote Similarity	NPD6924	Approved
0.6415	Remote Similarity	NPD4632	Approved
0.64	Remote Similarity	NPD5225	Approved
0.64	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD5224	Approved
0.64	Remote Similarity	NPD4633	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.6395	Remote Similarity	NPD6932	Approved
0.6392	Remote Similarity	NPD4697	Phase 3
0.6381	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7525	Registered
0.6364	Remote Similarity	NPD6404	Discontinued
0.6354	Remote Similarity	NPD5707	Approved
0.6353	Remote Similarity	NPD5275	Approved
0.6353	Remote Similarity	NPD4190	Phase 3
0.6344	Remote Similarity	NPD4518	Approved
0.6337	Remote Similarity	NPD5174	Approved
0.6337	Remote Similarity	NPD5175	Approved
0.633	Remote Similarity	NPD6335	Approved
0.6327	Remote Similarity	NPD4755	Approved
0.6322	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7145	Approved
0.6279	Remote Similarity	NPD6933	Approved
0.6275	Remote Similarity	NPD5141	Approved
0.6273	Remote Similarity	NPD7101	Approved
0.6273	Remote Similarity	NPD7100	Approved
0.6265	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD6939	Phase 2
0.6263	Remote Similarity	NPD5290	Discontinued
0.6262	Remote Similarity	NPD6858	Approved
0.6262	Remote Similarity	NPD7094	Approved
0.6239	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD6317	Approved
0.6238	Remote Similarity	NPD5091	Approved
0.6224	Remote Similarity	NPD7614	Phase 1
0.6211	Remote Similarity	NPD5785	Approved
0.6211	Remote Similarity	NPD4096	Approved
0.6207	Remote Similarity	NPD5776	Phase 2
0.6207	Remote Similarity	NPD6925	Approved
0.62	Remote Similarity	NPD4700	Approved
0.6182	Remote Similarity	NPD6314	Approved
0.6182	Remote Similarity	NPD6313	Approved
0.618	Remote Similarity	NPD7514	Phase 3
0.6154	Remote Similarity	NPD6412	Phase 2
0.6147	Remote Similarity	NPD6274	Approved
0.6146	Remote Similarity	NPD8034	Phase 2
0.6146	Remote Similarity	NPD8035	Phase 2
0.6136	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6902	Approved
0.6111	Remote Similarity	NPD4692	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