NPASS Compound

Structure

NPC182106 OpenBabel07101718232D 25 28 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 2.5981 -0.5000 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 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 -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 4.3301 -1.5000 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 3.4641 -1.0000 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 3.4641 -3.0000 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 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 1.7321 -1.0000 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 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 N 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 1 6 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 18 2 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 6 0 0 0 16 24 1 6 0 0 0 17 8 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 19 22 1 6 0 0 0 20 23 1 6 0 0 0 21 25 2 0 0 0 0 22 2 1 6 0 0 0 23 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	343.29
Volume:	386.652
LogP:	5.088
LogD:	4.312
LogS:	-4.134
# Rotatable Bonds:	1
TPSA:	20.31
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	4.433
Fsp3:	0.87
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:	-4.685
MDCK Permeability:	1.5128594895941205e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.068
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.116
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.389
Plasma Protein Binding (PPB):	56.890098571777344%
Volume Distribution (VD):	1.227
Pgp-substrate:	30.232112884521484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.316
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.958
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.725
CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.844
CYP3A4-substrate:	0.743

ADMET: Excretion

Clearance (CL):	19.908
Half-life (T1/2):	0.074

ADMET: Toxicity

hERG Blockers:	0.911
Human Hepatotoxicity (H-HT):	0.609
Drug-inuced Liver Injury (DILI):	0.834
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.537
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.961
Carcinogencity:	0.767
Eye Corrosion:	0.956
Eye Irritation:	0.169
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC182106

Natural Product ID:	NPC182106
*Common Name:**	E-Salignone
IUPAC Name:	(3S,5S,8R,9S,10S,13S,14S,17E)-3-(dimethylamino)-17-ethylidene-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-one
Synonyms:	E-Salignone
Standard InCHIKey:	MPLJLEJJNOUMDO-NIIFQURTSA-N
Standard InCHI:	InChI=1S/C23H37NO/c1-6-18-21(25)14-20-17-8-7-15-13-16(24(4)5)9-11-22(15,2)19(17)10-12-23(18,20)3/h6,15-17,19-20H,7-14H2,1-5H3/b18-6-/t15-,16-,17+,19-,20-,22-,23+/m0/s1
SMILES:	C/C=C1/C(=O)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CC[C@@H](C2)N(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087210
PubChem CID:	70688999
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003568] Androstane steroids

*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
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22804108]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13852	Pachysandra terminalis	Species	Buxaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	870.0	nM	PMID[575764]

☑ 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 NPC182106 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	115
0.1-0.2	1292
0.2-0.3	15832
0.3-0.4	13344
0.4-0.5	8272
0.5-0.6	3370
0.6-0.7	406
0.7-0.8	58
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC311769
0.9634	High Similarity	NPC259252
0.8966	High Similarity	NPC476752
0.8966	High Similarity	NPC476753
0.8864	High Similarity	NPC476754
0.814	Intermediate Similarity	NPC21667
0.8021	Intermediate Similarity	NPC152718
0.7979	Intermediate Similarity	NPC184033
0.7955	Intermediate Similarity	NPC147513
0.7895	Intermediate Similarity	NPC140685
0.7865	Intermediate Similarity	NPC157479
0.7835	Intermediate Similarity	NPC226509
0.7802	Intermediate Similarity	NPC249312
0.7732	Intermediate Similarity	NPC474001
0.7677	Intermediate Similarity	NPC469958
0.7653	Intermediate Similarity	NPC58200
0.7619	Intermediate Similarity	NPC293803
0.7614	Intermediate Similarity	NPC215474
0.76	Intermediate Similarity	NPC230677
0.759	Intermediate Similarity	NPC251705
0.759	Intermediate Similarity	NPC474228
0.759	Intermediate Similarity	NPC303613
0.7561	Intermediate Similarity	NPC282593
0.7561	Intermediate Similarity	NPC159577
0.7561	Intermediate Similarity	NPC265782
0.7561	Intermediate Similarity	NPC251929
0.7561	Intermediate Similarity	NPC35734
0.7561	Intermediate Similarity	NPC2634
0.75	Intermediate Similarity	NPC476904
0.75	Intermediate Similarity	NPC255021
0.75	Intermediate Similarity	NPC90150
0.747	Intermediate Similarity	NPC54123
0.747	Intermediate Similarity	NPC115023
0.747	Intermediate Similarity	NPC305501
0.747	Intermediate Similarity	NPC21773
0.747	Intermediate Similarity	NPC234707
0.7439	Intermediate Similarity	NPC139397
0.7412	Intermediate Similarity	NPC255650
0.7381	Intermediate Similarity	NPC470045
0.7381	Intermediate Similarity	NPC470044
0.7349	Intermediate Similarity	NPC477856
0.7349	Intermediate Similarity	NPC307176
0.7349	Intermediate Similarity	NPC214770
0.7349	Intermediate Similarity	NPC260040
0.7326	Intermediate Similarity	NPC69408
0.7317	Intermediate Similarity	NPC20610
0.7294	Intermediate Similarity	NPC329866
0.7294	Intermediate Similarity	NPC474797
0.7294	Intermediate Similarity	NPC474796
0.7294	Intermediate Similarity	NPC309852
0.7262	Intermediate Similarity	NPC110615
0.7229	Intermediate Similarity	NPC182815
0.7191	Intermediate Similarity	NPC250632
0.7191	Intermediate Similarity	NPC474509
0.7174	Intermediate Similarity	NPC152684
0.7143	Intermediate Similarity	NPC40574
0.7129	Intermediate Similarity	NPC476755
0.7126	Intermediate Similarity	NPC7214
0.7079	Intermediate Similarity	NPC211322
0.7073	Intermediate Similarity	NPC323005
0.7059	Intermediate Similarity	NPC265789
0.7059	Intermediate Similarity	NPC470078
0.7059	Intermediate Similarity	NPC225467
0.7059	Intermediate Similarity	NPC190035
0.7048	Intermediate Similarity	NPC175585
0.7024	Intermediate Similarity	NPC477857
0.7011	Intermediate Similarity	NPC473171
0.6989	Remote Similarity	NPC75810
0.6989	Remote Similarity	NPC34811
0.6989	Remote Similarity	NPC76283
0.6988	Remote Similarity	NPC20181
0.6988	Remote Similarity	NPC220210
0.6988	Remote Similarity	NPC176107
0.697	Remote Similarity	NPC247220
0.6952	Remote Similarity	NPC476918
0.6932	Remote Similarity	NPC469793
0.6932	Remote Similarity	NPC469796
0.6923	Remote Similarity	NPC195841
0.6923	Remote Similarity	NPC233256
0.6905	Remote Similarity	NPC310992
0.6905	Remote Similarity	NPC188292
0.6905	Remote Similarity	NPC142754
0.6905	Remote Similarity	NPC296697
0.6905	Remote Similarity	NPC260474
0.6905	Remote Similarity	NPC39157
0.6905	Remote Similarity	NPC82477
0.6889	Remote Similarity	NPC170793
0.6889	Remote Similarity	NPC90965
0.6882	Remote Similarity	NPC178025
0.6882	Remote Similarity	NPC16287
0.6882	Remote Similarity	NPC181743
0.6867	Remote Similarity	NPC189917
0.6867	Remote Similarity	NPC43300
0.6867	Remote Similarity	NPC107704
0.6867	Remote Similarity	NPC96812
0.6867	Remote Similarity	NPC92327
0.6867	Remote Similarity	NPC168824
0.6867	Remote Similarity	NPC39462
0.6863	Remote Similarity	NPC34193
0.686	Remote Similarity	NPC223187
0.686	Remote Similarity	NPC5701
0.6854	Remote Similarity	NPC91665
0.6848	Remote Similarity	NPC472239
0.6842	Remote Similarity	NPC43308
0.6829	Remote Similarity	NPC469662
0.6829	Remote Similarity	NPC212210
0.6827	Remote Similarity	NPC475239
0.6824	Remote Similarity	NPC286814
0.6824	Remote Similarity	NPC256846
0.6818	Remote Similarity	NPC125828
0.6809	Remote Similarity	NPC60350
0.6778	Remote Similarity	NPC115515
0.6774	Remote Similarity	NPC171639
0.6762	Remote Similarity	NPC476926
0.6762	Remote Similarity	NPC476328
0.6744	Remote Similarity	NPC473442
0.6744	Remote Similarity	NPC120167
0.6739	Remote Similarity	NPC118329
0.6739	Remote Similarity	NPC152039
0.6739	Remote Similarity	NPC257962
0.6739	Remote Similarity	NPC329782
0.6731	Remote Similarity	NPC98765
0.6707	Remote Similarity	NPC472306
0.6707	Remote Similarity	NPC197238
0.6707	Remote Similarity	NPC165695
0.6707	Remote Similarity	NPC202118
0.6706	Remote Similarity	NPC87141
0.6705	Remote Similarity	NPC159497
0.6705	Remote Similarity	NPC211641
0.6703	Remote Similarity	NPC215843
0.6698	Remote Similarity	NPC476756
0.6698	Remote Similarity	NPC244982
0.6697	Remote Similarity	NPC124358
0.6696	Remote Similarity	NPC474006
0.6667	Remote Similarity	NPC320514
0.6667	Remote Similarity	NPC469804
0.6667	Remote Similarity	NPC469805
0.6667	Remote Similarity	NPC476293
0.6667	Remote Similarity	NPC119329
0.6667	Remote Similarity	NPC100297
0.6667	Remote Similarity	NPC181204
0.6667	Remote Similarity	NPC142253
0.6667	Remote Similarity	NPC127582
0.6667	Remote Similarity	NPC472312
0.6667	Remote Similarity	NPC472867
0.6667	Remote Similarity	NPC3511
0.6667	Remote Similarity	NPC93778
0.6667	Remote Similarity	NPC25853
0.6667	Remote Similarity	NPC470557
0.6636	Remote Similarity	NPC24596
0.6636	Remote Similarity	NPC476276
0.6636	Remote Similarity	NPC476919
0.6636	Remote Similarity	NPC476920
0.6634	Remote Similarity	NPC476903
0.6632	Remote Similarity	NPC29447
0.663	Remote Similarity	NPC469798
0.663	Remote Similarity	NPC469797
0.663	Remote Similarity	NPC12035
0.6628	Remote Similarity	NPC138409
0.6627	Remote Similarity	NPC285371
0.6627	Remote Similarity	NPC475124
0.6625	Remote Similarity	NPC266295
0.6625	Remote Similarity	NPC94991
0.6607	Remote Similarity	NPC473573
0.6606	Remote Similarity	NPC143173
0.6604	Remote Similarity	NPC185929
0.6602	Remote Similarity	NPC128698
0.6602	Remote Similarity	NPC239768
0.6602	Remote Similarity	NPC477964
0.6596	Remote Similarity	NPC279639
0.6596	Remote Similarity	NPC474976
0.6596	Remote Similarity	NPC3856
0.6596	Remote Similarity	NPC474790
0.6593	Remote Similarity	NPC82635
0.6593	Remote Similarity	NPC469996
0.6593	Remote Similarity	NPC228911
0.6593	Remote Similarity	NPC470052
0.6591	Remote Similarity	NPC474488
0.6588	Remote Similarity	NPC475523
0.6585	Remote Similarity	NPC213152
0.6585	Remote Similarity	NPC60565
0.6562	Remote Similarity	NPC166458
0.6559	Remote Similarity	NPC473217
0.6556	Remote Similarity	NPC474463
0.6548	Remote Similarity	NPC251118
0.6543	Remote Similarity	NPC21781
0.6543	Remote Similarity	NPC472304
0.6543	Remote Similarity	NPC276764
0.6543	Remote Similarity	NPC259261
0.6526	Remote Similarity	NPC85774
0.6526	Remote Similarity	NPC214043
0.6526	Remote Similarity	NPC87552
0.6517	Remote Similarity	NPC219232
0.6517	Remote Similarity	NPC128346
0.6514	Remote Similarity	NPC63511
0.6512	Remote Similarity	NPC155198
0.6509	Remote Similarity	NPC476921
0.65	Remote Similarity	NPC247316
0.65	Remote Similarity	NPC115385
0.65	Remote Similarity	NPC230823

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 NPC182106 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	103
0.1-0.2	852
0.2-0.3	4170
0.3-0.4	2957
0.4-0.5	743
0.5-0.6	263
0.6-0.7	53
0.7-0.8	9
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
0.7561	Intermediate Similarity	NPD4691	Approved
0.7474	Intermediate Similarity	NPD5769	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4137	Phase 3
0.7349	Intermediate Similarity	NPD4747	Approved
0.7294	Intermediate Similarity	NPD4058	Approved
0.7143	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8028	Phase 2
0.7108	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5733	Approved
0.6897	Remote Similarity	NPD4687	Approved
0.6889	Remote Similarity	NPD7155	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5276	Approved
0.6667	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4221	Approved
0.6489	Remote Similarity	NPD4223	Phase 3
0.6458	Remote Similarity	NPD5329	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3617	Approved
0.6392	Remote Similarity	NPD7521	Approved
0.6392	Remote Similarity	NPD7146	Approved
0.6392	Remote Similarity	NPD6409	Approved
0.6392	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7334	Approved
0.6392	Remote Similarity	NPD6684	Approved
0.6392	Remote Similarity	NPD5330	Approved
0.6354	Remote Similarity	NPD3666	Approved
0.6354	Remote Similarity	NPD3133	Approved
0.6354	Remote Similarity	NPD4197	Approved
0.6354	Remote Similarity	NPD3665	Phase 1
0.6296	Remote Similarity	NPD7333	Discontinued
0.6263	Remote Similarity	NPD6672	Approved
0.6263	Remote Similarity	NPD6903	Approved
0.6263	Remote Similarity	NPD5737	Approved
0.6238	Remote Similarity	NPD6079	Approved
0.6224	Remote Similarity	NPD4689	Approved
0.6224	Remote Similarity	NPD3618	Phase 1
0.6224	Remote Similarity	NPD5205	Approved
0.6224	Remote Similarity	NPD4138	Approved
0.6224	Remote Similarity	NPD4693	Phase 3
0.6224	Remote Similarity	NPD5690	Phase 2
0.6224	Remote Similarity	NPD4690	Approved
0.6224	Remote Similarity	NPD4688	Approved
0.62	Remote Similarity	NPD6080	Approved
0.62	Remote Similarity	NPD6673	Approved
0.62	Remote Similarity	NPD6904	Approved
0.62	Remote Similarity	NPD5328	Approved
0.6198	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4786	Approved
0.6154	Remote Similarity	NPD7614	Phase 1
0.6154	Remote Similarity	NPD7732	Phase 3
0.6146	Remote Similarity	NPD3667	Approved
0.6139	Remote Similarity	NPD4096	Approved
0.6139	Remote Similarity	NPD6934	Discontinued
0.6132	Remote Similarity	NPD6404	Discontinued
0.6105	Remote Similarity	NPD4695	Discontinued
0.61	Remote Similarity	NPD5208	Approved
0.6095	Remote Similarity	NPD4657	Approved
0.6095	Remote Similarity	NPD4655	Approved
0.6082	Remote Similarity	NPD4788	Approved
0.6061	Remote Similarity	NPD6098	Approved
0.6061	Remote Similarity	NPD4694	Approved
0.6061	Remote Similarity	NPD5280	Approved
0.604	Remote Similarity	NPD4753	Phase 2
0.6024	Remote Similarity	NPD287	Approved
0.602	Remote Similarity	NPD3668	Phase 3
0.6019	Remote Similarity	NPD6024	Approved
0.6019	Remote Similarity	NPD6027	Approved
0.6	Remote Similarity	NPD4195	Approved
0.5962	Remote Similarity	NPD5771	Approved
0.5934	Remote Similarity	NPD5365	Phase 2
0.5922	Remote Similarity	NPD5693	Phase 1
0.5922	Remote Similarity	NPD6050	Approved
0.5905	Remote Similarity	NPD4629	Approved
0.5905	Remote Similarity	NPD5210	Approved
0.5905	Remote Similarity	NPD4094	Approved
0.5905	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4519	Discontinued
0.59	Remote Similarity	NPD4623	Approved
0.59	Remote Similarity	NPD5279	Phase 3
0.5895	Remote Similarity	NPD4776	Phase 2
0.5895	Remote Similarity	NPD4777	Suspended
0.5882	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD4202	Approved
0.5856	Remote Similarity	NPD6920	Discontinued
0.5849	Remote Similarity	NPD5222	Approved
0.5849	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5221	Approved
0.5842	Remote Similarity	NPD3573	Approved
0.5833	Remote Similarity	NPD6909	Approved
0.5833	Remote Similarity	NPD6908	Approved
0.5825	Remote Similarity	NPD5207	Approved
0.5825	Remote Similarity	NPD5692	Phase 3
0.5824	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD6939	Phase 2
0.581	Remote Similarity	NPD6001	Approved
0.5794	Remote Similarity	NPD6083	Phase 2
0.5794	Remote Similarity	NPD5173	Approved
0.5794	Remote Similarity	NPD6084	Phase 2
0.5769	Remote Similarity	NPD5694	Approved
0.5769	Remote Similarity	NPD5281	Approved
0.5769	Remote Similarity	NPD7515	Phase 2
0.5769	Remote Similarity	NPD5284	Approved
0.5752	Remote Similarity	NPD6415	Discontinued
0.5727	Remote Similarity	NPD2196	Discontinued
0.5727	Remote Similarity	NPD2193	Phase 2
0.5727	Remote Similarity	NPD2648	Phase 3
0.5714	Remote Similarity	NPD5133	Approved
0.5714	Remote Similarity	NPD2192	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD4692	Approved
0.5714	Remote Similarity	NPD2197	Approved
0.5714	Remote Similarity	NPD4139	Approved
0.5701	Remote Similarity	NPD4697	Phase 3
0.5688	Remote Similarity	NPD5286	Approved
0.5688	Remote Similarity	NPD5285	Approved
0.5688	Remote Similarity	NPD4696	Approved
0.568	Remote Similarity	NPD8336	Approved
0.568	Remote Similarity	NPD8337	Approved
0.566	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7900	Approved
0.566	Remote Similarity	NPD7748	Approved
0.5657	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD4755	Approved
0.5636	Remote Similarity	NPD5223	Approved
0.5607	Remote Similarity	NPD5654	Approved
0.5607	Remote Similarity	NPD5695	Phase 3

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