NPASS Compound

Structure

NPC105197 OpenBabel07101719522D 28 31 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 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 2.4688 6.8916 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 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 3.4980 4.4543 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 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 2.8289 5.1974 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 1.8508 4.9895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1379 6.1485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 28 1 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 1 1 1 0 0 0 16 20 1 0 0 0 0 17 24 1 0 0 0 0 18 26 2 0 0 0 0 19 7 1 6 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 25 1 1 0 0 0 21 25 1 1 0 0 0 22 24 1 1 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 24 2 1 1 0 0 0 25 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.25
Volume:	419.919
LogP:	5.189
LogD:	4.709
LogS:	-4.927
# Rotatable Bonds:	4
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	4.52
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.583
MDCK Permeability:	4.960965088685043e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.214
30% Bioavailability (F30%):	0.191

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12
Plasma Protein Binding (PPB):	94.76058197021484%
Volume Distribution (VD):	0.91
Pgp-substrate:	3.57865834236145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.333
CYP1A2-substrate:	0.264
CYP2C19-inhibitor:	0.788
CYP2C19-substrate:	0.722
CYP2C9-inhibitor:	0.557
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.47
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.944
CYP3A4-substrate:	0.833

ADMET: Excretion

Clearance (CL):	10.721
Half-life (T1/2):	0.223

ADMET: Toxicity

hERG Blockers:	0.233
Human Hepatotoxicity (H-HT):	0.562
Drug-inuced Liver Injury (DILI):	0.333
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.974
Carcinogencity:	0.77
Eye Corrosion:	0.311
Eye Irritation:	0.13
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC105197

Natural Product ID:	NPC105197
*Common Name:**	Methyl 3-Oxochola-4,22-Dien-24-Oate
IUPAC Name:	methyl (E,4R)-4-[(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]pent-2-enoate
Synonyms:
Standard InCHIKey:	RRYFVLJZIKHVMF-QEALGLRWSA-N
Standard InCHI:	InChI=1S/C25H34O3/c1-16(5-10-23(27)28-4)20-8-9-21-19-7-6-17-15-18(26)11-13-24(17,2)22(19)12-14-25(20,21)3/h5,10-11,13,15-16,19-22H,6-9,12,14H2,1-4H3/b10-5+/t16-,19+,20-,21+,22+,24+,25-/m1/s1
SMILES:	C[C@H](/C=C/C(=O)OC)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479686
PubChem CID:	10643638
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
NPO32820	octocorals	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10579868]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2540	Organism	Balanus amphitrite	Balanus amphitrite	LD100	=	100.0	ug ml-1	PMID[498299]

☑ 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 NPC105197 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	165
0.1-0.2	1495
0.2-0.3	7748
0.3-0.4	15900
0.4-0.5	7849
0.5-0.6	6546
0.6-0.7	2631
0.7-0.8	337
0.8-0.85	16
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC190211
0.9189	High Similarity	NPC474463
0.8675	High Similarity	NPC177141
0.8625	High Similarity	NPC474976
0.8625	High Similarity	NPC474790
0.8611	High Similarity	NPC176107
0.8571	High Similarity	NPC273199
0.8472	Intermediate Similarity	NPC185587
0.8472	Intermediate Similarity	NPC92327
0.8462	Intermediate Similarity	NPC470052
0.8312	Intermediate Similarity	NPC65650
0.8272	Intermediate Similarity	NPC472239
0.8235	Intermediate Similarity	NPC474844
0.8214	Intermediate Similarity	NPC163016
0.8214	Intermediate Similarity	NPC75315
0.8182	Intermediate Similarity	NPC20025
0.8182	Intermediate Similarity	NPC281134
0.8101	Intermediate Similarity	NPC470557
0.8052	Intermediate Similarity	NPC251705
0.8052	Intermediate Similarity	NPC303613
0.8052	Intermediate Similarity	NPC474228
0.8049	Intermediate Similarity	NPC472867
0.8049	Intermediate Similarity	NPC142253
0.8049	Intermediate Similarity	NPC100297
0.8049	Intermediate Similarity	NPC3511
0.7975	Intermediate Similarity	NPC69408
0.7975	Intermediate Similarity	NPC4509
0.7973	Intermediate Similarity	NPC176171
0.7952	Intermediate Similarity	NPC118423
0.7949	Intermediate Similarity	NPC309852
0.7922	Intermediate Similarity	NPC115023
0.7922	Intermediate Similarity	NPC54123
0.7922	Intermediate Similarity	NPC234707
0.7922	Intermediate Similarity	NPC305501
0.7882	Intermediate Similarity	NPC472863
0.7857	Intermediate Similarity	NPC178025
0.7857	Intermediate Similarity	NPC16287
0.7857	Intermediate Similarity	NPC181743
0.7857	Intermediate Similarity	NPC87552
0.7848	Intermediate Similarity	NPC293803
0.7831	Intermediate Similarity	NPC268122
0.7831	Intermediate Similarity	NPC469805
0.7831	Intermediate Similarity	NPC94200
0.7831	Intermediate Similarity	NPC469804
0.7821	Intermediate Similarity	NPC276336
0.7821	Intermediate Similarity	NPC470044
0.7821	Intermediate Similarity	NPC470045
0.7816	Intermediate Similarity	NPC285982
0.7805	Intermediate Similarity	NPC474509
0.7792	Intermediate Similarity	NPC2634
0.7792	Intermediate Similarity	NPC35734
0.7792	Intermediate Similarity	NPC307176
0.7792	Intermediate Similarity	NPC282593
0.7792	Intermediate Similarity	NPC265782
0.7792	Intermediate Similarity	NPC251929
0.7792	Intermediate Similarity	NPC159577
0.7791	Intermediate Similarity	NPC476293
0.7778	Intermediate Similarity	NPC33473
0.7765	Intermediate Similarity	NPC29447
0.7765	Intermediate Similarity	NPC8571
0.7765	Intermediate Similarity	NPC60350
0.7742	Intermediate Similarity	NPC310981
0.7738	Intermediate Similarity	NPC3856
0.7738	Intermediate Similarity	NPC279639
0.7738	Intermediate Similarity	NPC470046
0.7738	Intermediate Similarity	NPC470047
0.7733	Intermediate Similarity	NPC242945
0.7733	Intermediate Similarity	NPC259156
0.7727	Intermediate Similarity	NPC302280
0.7722	Intermediate Similarity	NPC255021
0.7703	Intermediate Similarity	NPC329698
0.7692	Intermediate Similarity	NPC181587
0.7683	Intermediate Similarity	NPC44083
0.7683	Intermediate Similarity	NPC153987
0.7674	Intermediate Similarity	NPC168248
0.7662	Intermediate Similarity	NPC182815
0.7662	Intermediate Similarity	NPC139397
0.764	Intermediate Similarity	NPC177641
0.764	Intermediate Similarity	NPC218301
0.7625	Intermediate Similarity	NPC255650
0.7625	Intermediate Similarity	NPC476346
0.7619	Intermediate Similarity	NPC320514
0.7619	Intermediate Similarity	NPC469806
0.7619	Intermediate Similarity	NPC327969
0.7619	Intermediate Similarity	NPC321289
0.7619	Intermediate Similarity	NPC469799
0.7619	Intermediate Similarity	NPC471218
0.7614	Intermediate Similarity	NPC472240
0.7614	Intermediate Similarity	NPC262858
0.7614	Intermediate Similarity	NPC146554
0.7614	Intermediate Similarity	NPC262043
0.76	Intermediate Similarity	NPC107258
0.759	Intermediate Similarity	NPC469797
0.759	Intermediate Similarity	NPC469798
0.7586	Intermediate Similarity	NPC477228
0.7582	Intermediate Similarity	NPC171395
0.7564	Intermediate Similarity	NPC260040
0.7558	Intermediate Similarity	NPC474013
0.7558	Intermediate Similarity	NPC189311
0.7556	Intermediate Similarity	NPC38232
0.7532	Intermediate Similarity	NPC20610
0.7531	Intermediate Similarity	NPC40353
0.7529	Intermediate Similarity	NPC30502
0.7529	Intermediate Similarity	NPC42476
0.7527	Intermediate Similarity	NPC98868
0.75	Intermediate Similarity	NPC474796
0.75	Intermediate Similarity	NPC329866
0.75	Intermediate Similarity	NPC60772
0.75	Intermediate Similarity	NPC474797
0.7473	Intermediate Similarity	NPC201725
0.7473	Intermediate Similarity	NPC471994
0.7473	Intermediate Similarity	NPC120351
0.7473	Intermediate Similarity	NPC128488
0.7473	Intermediate Similarity	NPC166143
0.7473	Intermediate Similarity	NPC304968
0.7471	Intermediate Similarity	NPC470050
0.7471	Intermediate Similarity	NPC470051
0.7471	Intermediate Similarity	NPC286153
0.7471	Intermediate Similarity	NPC195640
0.747	Intermediate Similarity	NPC170793
0.747	Intermediate Similarity	NPC90965
0.7468	Intermediate Similarity	NPC470078
0.7444	Intermediate Similarity	NPC474018
0.7444	Intermediate Similarity	NPC23217
0.7444	Intermediate Similarity	NPC234335
0.7444	Intermediate Similarity	NPC473986
0.7442	Intermediate Similarity	NPC475100
0.7442	Intermediate Similarity	NPC318515
0.7442	Intermediate Similarity	NPC33913
0.7442	Intermediate Similarity	NPC320801
0.7439	Intermediate Similarity	NPC472300
0.7439	Intermediate Similarity	NPC91665
0.7423	Intermediate Similarity	NPC127790
0.7419	Intermediate Similarity	NPC253826
0.7416	Intermediate Similarity	NPC66344
0.7412	Intermediate Similarity	NPC16321
0.7407	Intermediate Similarity	NPC473171
0.7391	Intermediate Similarity	NPC293052
0.7391	Intermediate Similarity	NPC474909
0.7386	Intermediate Similarity	NPC136948
0.7375	Intermediate Similarity	NPC180015
0.7375	Intermediate Similarity	NPC56747
0.7375	Intermediate Similarity	NPC130016
0.7375	Intermediate Similarity	NPC109576
0.7368	Intermediate Similarity	NPC194028
0.7368	Intermediate Similarity	NPC168319
0.7363	Intermediate Similarity	NPC229976
0.7363	Intermediate Similarity	NPC472871
0.7356	Intermediate Similarity	NPC329630
0.7356	Intermediate Similarity	NPC472442
0.7356	Intermediate Similarity	NPC470048
0.7356	Intermediate Similarity	NPC470223
0.7356	Intermediate Similarity	NPC323765
0.7349	Intermediate Similarity	NPC469996
0.7349	Intermediate Similarity	NPC82635
0.7347	Intermediate Similarity	NPC475294
0.7342	Intermediate Similarity	NPC40574
0.734	Intermediate Similarity	NPC108368
0.734	Intermediate Similarity	NPC57079
0.7333	Intermediate Similarity	NPC476437
0.7333	Intermediate Similarity	NPC476369
0.7326	Intermediate Similarity	NPC477124
0.7326	Intermediate Similarity	NPC472440
0.7326	Intermediate Similarity	NPC469
0.7326	Intermediate Similarity	NPC41539
0.732	Intermediate Similarity	NPC189616
0.7317	Intermediate Similarity	NPC473223
0.7317	Intermediate Similarity	NPC469793
0.7317	Intermediate Similarity	NPC469796
0.7317	Intermediate Similarity	NPC27205
0.7312	Intermediate Similarity	NPC58052
0.7312	Intermediate Similarity	NPC111684
0.7312	Intermediate Similarity	NPC190713
0.7308	Intermediate Similarity	NPC260474
0.7308	Intermediate Similarity	NPC188292
0.7303	Intermediate Similarity	NPC473879
0.7303	Intermediate Similarity	NPC472302
0.7303	Intermediate Similarity	NPC472870
0.7303	Intermediate Similarity	NPC196407
0.7294	Intermediate Similarity	NPC147066
0.7294	Intermediate Similarity	NPC6434
0.7294	Intermediate Similarity	NPC82986
0.7294	Intermediate Similarity	NPC474759
0.7294	Intermediate Similarity	NPC474731
0.7294	Intermediate Similarity	NPC477372
0.7294	Intermediate Similarity	NPC474752
0.7294	Intermediate Similarity	NPC7505
0.7294	Intermediate Similarity	NPC474683
0.7273	Intermediate Similarity	NPC264127
0.7273	Intermediate Similarity	NPC323005
0.7273	Intermediate Similarity	NPC220478
0.7273	Intermediate Similarity	NPC255781
0.7263	Intermediate Similarity	NPC201406
0.7262	Intermediate Similarity	NPC242767
0.7253	Intermediate Similarity	NPC74296
0.7253	Intermediate Similarity	NPC204341
0.7253	Intermediate Similarity	NPC110923
0.7253	Intermediate Similarity	NPC212948
0.7253	Intermediate Similarity	NPC190442
0.725	Intermediate Similarity	NPC257618

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 NPC105197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1478
0.2-0.3	4770
0.3-0.4	2058
0.4-0.5	328
0.5-0.6	177
0.6-0.7	162
0.7-0.8	30
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
0.7792	Intermediate Similarity	NPD4747	Approved
0.7792	Intermediate Similarity	NPD4691	Approved
0.7722	Intermediate Similarity	NPD4058	Approved
0.7662	Intermediate Similarity	NPD4137	Phase 3
0.7614	Intermediate Similarity	NPD6051	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD4687	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD5733	Approved
0.7471	Intermediate Similarity	NPD6684	Approved
0.7471	Intermediate Similarity	NPD7334	Approved
0.7471	Intermediate Similarity	NPD7521	Approved
0.7471	Intermediate Similarity	NPD5330	Approved
0.7471	Intermediate Similarity	NPD6409	Approved
0.7471	Intermediate Similarity	NPD7146	Approved
0.747	Intermediate Similarity	NPD4195	Approved
0.7444	Intermediate Similarity	NPD5693	Phase 1
0.7303	Intermediate Similarity	NPD6903	Approved
0.7303	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5276	Approved
0.7237	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6080	Approved
0.7222	Intermediate Similarity	NPD6904	Approved
0.7222	Intermediate Similarity	NPD6673	Approved
0.7209	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5208	Approved
0.7089	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6098	Approved
0.7021	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7638	Approved
0.6966	Remote Similarity	NPD1694	Approved
0.6957	Remote Similarity	NPD5207	Approved
0.6907	Remote Similarity	NPD7639	Approved
0.6907	Remote Similarity	NPD7640	Approved
0.6882	Remote Similarity	NPD6079	Approved
0.6882	Remote Similarity	NPD6050	Approved
0.6882	Remote Similarity	NPD5694	Approved
0.6875	Remote Similarity	NPD6083	Phase 2
0.6875	Remote Similarity	NPD6084	Phase 2
0.6818	Remote Similarity	NPD4223	Phase 3
0.6818	Remote Similarity	NPD4221	Approved
0.6813	Remote Similarity	NPD3573	Approved
0.6809	Remote Similarity	NPD6399	Phase 3
0.6778	Remote Similarity	NPD5329	Approved
0.6774	Remote Similarity	NPD5692	Phase 3
0.6753	Remote Similarity	NPD4193	Approved
0.6753	Remote Similarity	NPD4194	Approved
0.6753	Remote Similarity	NPD4192	Approved
0.6753	Remote Similarity	NPD4191	Approved
0.6742	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6001	Approved
0.6729	Remote Similarity	NPD7115	Discovery
0.6703	Remote Similarity	NPD5690	Phase 2
0.6702	Remote Similarity	NPD5284	Approved
0.6702	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6633	Remote Similarity	NPD5696	Approved
0.6627	Remote Similarity	NPD4243	Approved
0.6602	Remote Similarity	NPD6899	Approved
0.6602	Remote Similarity	NPD6881	Approved
0.6588	Remote Similarity	NPD6942	Approved
0.6588	Remote Similarity	NPD7339	Approved
0.6526	Remote Similarity	NPD7637	Suspended
0.6522	Remote Similarity	NPD4693	Phase 3
0.6522	Remote Similarity	NPD3618	Phase 1
0.6522	Remote Similarity	NPD4138	Approved
0.6522	Remote Similarity	NPD4519	Discontinued
0.6522	Remote Similarity	NPD5205	Approved
0.6522	Remote Similarity	NPD4623	Approved
0.6522	Remote Similarity	NPD4689	Approved
0.6522	Remote Similarity	NPD4688	Approved
0.6522	Remote Similarity	NPD4690	Approved
0.6505	Remote Similarity	NPD6614	Approved
0.6505	Remote Similarity	NPD5697	Approved
0.6495	Remote Similarity	NPD5210	Approved
0.6495	Remote Similarity	NPD4629	Approved
0.6489	Remote Similarity	NPD4753	Phase 2
0.6484	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7102	Approved
0.6476	Remote Similarity	NPD6883	Approved
0.6476	Remote Similarity	NPD7290	Approved
0.6444	Remote Similarity	NPD5209	Approved
0.6444	Remote Similarity	NPD3667	Approved
0.6442	Remote Similarity	NPD6011	Approved
0.6429	Remote Similarity	NPD5222	Approved
0.6429	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5221	Approved
0.6421	Remote Similarity	NPD5785	Approved
0.6415	Remote Similarity	NPD8130	Phase 1
0.6415	Remote Similarity	NPD6617	Approved
0.6415	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD6649	Approved
0.6415	Remote Similarity	NPD6869	Approved
0.6415	Remote Similarity	NPD6650	Approved
0.6408	Remote Similarity	NPD6402	Approved
0.6408	Remote Similarity	NPD7128	Approved
0.6408	Remote Similarity	NPD5739	Approved
0.6408	Remote Similarity	NPD6675	Approved
0.64	Remote Similarity	NPD6404	Discontinued
0.6395	Remote Similarity	NPD8039	Approved
0.6392	Remote Similarity	NPD7748	Approved
0.6392	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7900	Approved
0.6381	Remote Similarity	NPD6013	Approved
0.6381	Remote Similarity	NPD6012	Approved
0.6381	Remote Similarity	NPD6014	Approved
0.6373	Remote Similarity	NPD6052	Approved
0.6364	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD3617	Approved
0.6355	Remote Similarity	NPD6882	Approved
0.6355	Remote Similarity	NPD8297	Approved
0.6354	Remote Similarity	NPD7515	Phase 2
0.6344	Remote Similarity	NPD5279	Phase 3
0.6344	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4694	Approved
0.6344	Remote Similarity	NPD5280	Approved
0.6339	Remote Similarity	NPD7503	Approved
0.6333	Remote Similarity	NPD8028	Phase 2
0.6327	Remote Similarity	NPD5654	Approved
0.6322	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7143	Approved
0.631	Remote Similarity	NPD7144	Approved
0.6304	Remote Similarity	NPD3668	Phase 3
0.63	Remote Similarity	NPD4225	Approved
0.6296	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4202	Approved
0.6286	Remote Similarity	NPD7320	Approved
0.6275	Remote Similarity	NPD5211	Phase 2
0.6275	Remote Similarity	NPD7632	Discontinued
0.6263	Remote Similarity	NPD7732	Phase 3
0.625	Remote Similarity	NPD6008	Approved
0.6238	Remote Similarity	NPD4696	Approved
0.6238	Remote Similarity	NPD5286	Approved
0.6238	Remote Similarity	NPD5285	Approved
0.6235	Remote Similarity	NPD7152	Approved
0.6235	Remote Similarity	NPD7150	Approved
0.6235	Remote Similarity	NPD7151	Approved
0.6226	Remote Similarity	NPD6372	Approved
0.6226	Remote Similarity	NPD6373	Approved
0.6224	Remote Similarity	NPD5707	Approved
0.6222	Remote Similarity	NPD4695	Discontinued
0.6222	Remote Similarity	NPD7514	Phase 3
0.6222	Remote Similarity	NPD7525	Registered
0.6207	Remote Similarity	NPD4190	Phase 3
0.6207	Remote Similarity	NPD5275	Approved
0.62	Remote Similarity	NPD7902	Approved
0.62	Remote Similarity	NPD5959	Approved
0.6196	Remote Similarity	NPD4788	Approved
0.619	Remote Similarity	NPD5701	Approved
0.619	Remote Similarity	NPD6922	Approved
0.619	Remote Similarity	NPD6923	Approved
0.6182	Remote Similarity	NPD6868	Approved
0.618	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.618	Remote Similarity	NPD7145	Approved
0.6176	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD6902	Approved
0.6154	Remote Similarity	NPD5141	Approved
0.6154	Remote Similarity	NPD287	Approved
0.6147	Remote Similarity	NPD4632	Approved
0.6146	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5290	Discontinued
0.6132	Remote Similarity	NPD6686	Approved
0.6118	Remote Similarity	NPD6939	Phase 2
0.6118	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5224	Approved
0.6117	Remote Similarity	NPD5225	Approved
0.6117	Remote Similarity	NPD5226	Approved
0.6117	Remote Similarity	NPD4633	Approved
0.6111	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4697	Phase 3
0.6092	Remote Similarity	NPD6924	Approved
0.6092	Remote Similarity	NPD6926	Approved
0.6071	Remote Similarity	NPD6335	Approved
0.6071	Remote Similarity	NPD7328	Approved
0.6071	Remote Similarity	NPD7327	Approved
0.6067	Remote Similarity	NPD5776	Phase 2
0.6067	Remote Similarity	NPD6932	Approved
0.6067	Remote Similarity	NPD6925	Approved
0.6064	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5175	Approved
0.6058	Remote Similarity	NPD5174	Approved
0.6044	Remote Similarity	NPD7332	Phase 2
0.604	Remote Similarity	NPD4755	Approved
0.6018	Remote Similarity	NPD7101	Approved
0.6018	Remote Similarity	NPD7100	Approved
0.6018	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD7094	Approved
0.6	Remote Similarity	NPD6858	Approved
0.5982	Remote Similarity	NPD6009	Approved
0.5982	Remote Similarity	NPD6317	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