NPASS Compound

Structure

NPC94991 OpenBabel07101719152D 21 22 0 0 1 0 0 0 0 0999 V2000 -2.4627 -2.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8737 -2.9334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5551 -3.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0350 1.7434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9021 -0.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4143 -0.8283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0426 -1.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2251 0.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 -2.3843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3632 -1.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5794 -0.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9174 0.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5632 1.1131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4692 -2.1301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2281 -2.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5350 0.8774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0712 -1.2127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0951 -0.9955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6182 0.7861 0.0000 C 0 0 0 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 0.0381 1.6006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 17 2 0 0 0 0 17 18 1 0 0 0 0 18 20 1 6 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	335.608
LogP:	5.39
LogD:	4.267
LogS:	-5.199
# Rotatable Bonds:	0
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	4.59
Fsp3:	0.65
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:	-4.606
MDCK Permeability:	1.912569314299617e-05
Pgp-inhibitor:	0.746
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.902

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192
Plasma Protein Binding (PPB):	97.95343780517578%
Volume Distribution (VD):	3.592
Pgp-substrate:	2.5357747077941895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.25
CYP1A2-substrate:	0.473
CYP2C19-inhibitor:	0.427
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.593
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.709
CYP3A4-inhibitor:	0.529
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	10.184
Half-life (T1/2):	0.824

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.418
Drug-inuced Liver Injury (DILI):	0.13
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.093
Skin Sensitization:	0.936
Carcinogencity:	0.661
Eye Corrosion:	0.752
Eye Irritation:	0.948
Respiratory Toxicity:	0.665

Download Data

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

Natural Product: NPC94991

Natural Product ID:	NPC94991
*Common Name:**	Eduenone
IUPAC Name:	(3aR,5Z,9Z,12aR)-3a,6,10-trimethyl-1-propan-2-ylidene-3,7,8,11,12,12a-hexahydro-2H-cyclopenta[11]annulen-4-one
Synonyms:	Eduenone
Standard InCHIKey:	UPOREMYWIBIKTQ-DJIMEFRCSA-N
Standard InCHI:	InChI=1S/C20H30O/c1-14(2)17-11-12-20(5)18(17)10-9-15(3)7-6-8-16(4)13-19(20)21/h7,13,18H,6,8-12H2,1-5H3/b15-7-,16-13-/t18-,20-/m1/s1
SMILES:	CC(=C1CC[C@]2(C)[C@@H]1CC/C(=CCC/C(=CC2=O)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449497
PubChem CID:	10424127
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane diterpenoids

*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
NPO22554	Eunicea laciniata	Species	Plexauridae	Eukaryota	n.a.	Caribbean	n.a.	PMID[7769391]
NPO22554	Eunicea laciniata	Species	Plexauridae	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
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	50.0	ug.mL-1	PMID[506757]

☑ 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 NPC94991 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	200
0.1-0.2	2901
0.2-0.3	16365
0.3-0.4	11562
0.4-0.5	7073
0.5-0.6	3576
0.6-0.7	845
0.7-0.8	138
0.8-0.85	16
0.85-0.9	7
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC266295
0.9818	High Similarity	NPC259261
0.9643	High Similarity	NPC25853
0.9455	High Similarity	NPC49575
0.9455	High Similarity	NPC55004
0.9455	High Similarity	NPC267626
0.9455	High Similarity	NPC230823
0.9286	High Similarity	NPC30215
0.9153	High Similarity	NPC473902
0.8983	High Similarity	NPC165695
0.8833	High Similarity	NPC212210
0.8814	High Similarity	NPC475795
0.8814	High Similarity	NPC97322
0.8814	High Similarity	NPC213152
0.8667	High Similarity	NPC32285
0.8596	High Similarity	NPC20603
0.8475	Intermediate Similarity	NPC143834
0.8475	Intermediate Similarity	NPC285594
0.8475	Intermediate Similarity	NPC96551
0.8448	Intermediate Similarity	NPC115385
0.8438	Intermediate Similarity	NPC139397
0.8413	Intermediate Similarity	NPC475523
0.8393	Intermediate Similarity	NPC474141
0.8333	Intermediate Similarity	NPC127582
0.8308	Intermediate Similarity	NPC307176
0.8308	Intermediate Similarity	NPC260040
0.8308	Intermediate Similarity	NPC2634
0.8308	Intermediate Similarity	NPC282593
0.8308	Intermediate Similarity	NPC35734
0.8308	Intermediate Similarity	NPC265782
0.8308	Intermediate Similarity	NPC251929
0.8308	Intermediate Similarity	NPC159577
0.8281	Intermediate Similarity	NPC469688
0.8182	Intermediate Similarity	NPC115023
0.8182	Intermediate Similarity	NPC181204
0.8182	Intermediate Similarity	NPC54123
0.8154	Intermediate Similarity	NPC162867
0.8154	Intermediate Similarity	NPC61702
0.8136	Intermediate Similarity	NPC193695
0.8103	Intermediate Similarity	NPC275472
0.8095	Intermediate Similarity	NPC251118
0.807	Intermediate Similarity	NPC268564
0.807	Intermediate Similarity	NPC296311
0.8065	Intermediate Similarity	NPC472306
0.8065	Intermediate Similarity	NPC167256
0.806	Intermediate Similarity	NPC303613
0.806	Intermediate Similarity	NPC470044
0.806	Intermediate Similarity	NPC251705
0.806	Intermediate Similarity	NPC474228
0.806	Intermediate Similarity	NPC470045
0.8036	Intermediate Similarity	NPC27438
0.8	Intermediate Similarity	NPC56905
0.8	Intermediate Similarity	NPC20610
0.8	Intermediate Similarity	NPC27610
0.7969	Intermediate Similarity	NPC323005
0.7941	Intermediate Similarity	NPC474797
0.7941	Intermediate Similarity	NPC309852
0.7941	Intermediate Similarity	NPC474796
0.7941	Intermediate Similarity	NPC329866
0.7941	Intermediate Similarity	NPC469691
0.7941	Intermediate Similarity	NPC167049
0.7937	Intermediate Similarity	NPC285371
0.7937	Intermediate Similarity	NPC475124
0.7937	Intermediate Similarity	NPC6697
0.7931	Intermediate Similarity	NPC63396
0.7931	Intermediate Similarity	NPC202850
0.791	Intermediate Similarity	NPC234707
0.791	Intermediate Similarity	NPC5701
0.7903	Intermediate Similarity	NPC60565
0.7879	Intermediate Similarity	NPC469677
0.7879	Intermediate Similarity	NPC256846
0.7879	Intermediate Similarity	NPC182815
0.7869	Intermediate Similarity	NPC276764
0.7869	Intermediate Similarity	NPC472304
0.7857	Intermediate Similarity	NPC32351
0.7833	Intermediate Similarity	NPC192427
0.7826	Intermediate Similarity	NPC251435
0.7826	Intermediate Similarity	NPC293803
0.7778	Intermediate Similarity	NPC202118
0.7778	Intermediate Similarity	NPC197238
0.7778	Intermediate Similarity	NPC288253
0.7761	Intermediate Similarity	NPC214770
0.7761	Intermediate Similarity	NPC477856
0.7759	Intermediate Similarity	NPC45283
0.7727	Intermediate Similarity	NPC188292
0.7727	Intermediate Similarity	NPC87141
0.7727	Intermediate Similarity	NPC469679
0.7727	Intermediate Similarity	NPC310992
0.7727	Intermediate Similarity	NPC260474
0.7727	Intermediate Similarity	NPC155198
0.7719	Intermediate Similarity	NPC64866
0.7719	Intermediate Similarity	NPC236623
0.7714	Intermediate Similarity	NPC469796
0.7714	Intermediate Similarity	NPC469646
0.7714	Intermediate Similarity	NPC469793
0.7714	Intermediate Similarity	NPC69408
0.7705	Intermediate Similarity	NPC311852
0.7705	Intermediate Similarity	NPC170799
0.7705	Intermediate Similarity	NPC308108
0.7681	Intermediate Similarity	NPC255021
0.7679	Intermediate Similarity	NPC145311
0.7667	Intermediate Similarity	NPC473733
0.7656	Intermediate Similarity	NPC469662
0.7647	Intermediate Similarity	NPC305501
0.7647	Intermediate Similarity	NPC470078
0.7636	Intermediate Similarity	NPC8610
0.7636	Intermediate Similarity	NPC262558
0.7586	Intermediate Similarity	NPC471751
0.7571	Intermediate Similarity	NPC469678
0.7571	Intermediate Similarity	NPC469669
0.7571	Intermediate Similarity	NPC77501
0.7571	Intermediate Similarity	NPC255650
0.7571	Intermediate Similarity	NPC473171
0.7571	Intermediate Similarity	NPC475771
0.7544	Intermediate Similarity	NPC116906
0.7538	Intermediate Similarity	NPC470329
0.7536	Intermediate Similarity	NPC92909
0.7536	Intermediate Similarity	NPC107783
0.75	Intermediate Similarity	NPC228911
0.75	Intermediate Similarity	NPC246722
0.75	Intermediate Similarity	NPC151045
0.75	Intermediate Similarity	NPC40574
0.75	Intermediate Similarity	NPC200258
0.746	Intermediate Similarity	NPC270042
0.7458	Intermediate Similarity	NPC23117
0.7424	Intermediate Similarity	NPC176171
0.7424	Intermediate Similarity	NPC92327
0.7419	Intermediate Similarity	NPC60772
0.7397	Intermediate Similarity	NPC469690
0.7397	Intermediate Similarity	NPC90965
0.7397	Intermediate Similarity	NPC170793
0.7391	Intermediate Similarity	NPC133253
0.7391	Intermediate Similarity	NPC223187
0.7391	Intermediate Similarity	NPC190035
0.7391	Intermediate Similarity	NPC304983
0.7385	Intermediate Similarity	NPC4638
0.7333	Intermediate Similarity	NPC95581
0.7324	Intermediate Similarity	NPC474011
0.7321	Intermediate Similarity	NPC100380
0.7321	Intermediate Similarity	NPC236355
0.7321	Intermediate Similarity	NPC14917
0.7321	Intermediate Similarity	NPC4079
0.7313	Intermediate Similarity	NPC176107
0.7297	Intermediate Similarity	NPC474509
0.7286	Intermediate Similarity	NPC130016
0.7286	Intermediate Similarity	NPC300940
0.7286	Intermediate Similarity	NPC109576
0.7286	Intermediate Similarity	NPC180015
0.7286	Intermediate Similarity	NPC56747
0.7273	Intermediate Similarity	NPC183422
0.726	Intermediate Similarity	NPC469996
0.7241	Intermediate Similarity	NPC228776
0.7241	Intermediate Similarity	NPC163984
0.7241	Intermediate Similarity	NPC58970
0.7241	Intermediate Similarity	NPC176819
0.7222	Intermediate Similarity	NPC215481
0.7222	Intermediate Similarity	NPC226242
0.7213	Intermediate Similarity	NPC188789
0.7206	Intermediate Similarity	NPC39157
0.7206	Intermediate Similarity	NPC82477
0.7206	Intermediate Similarity	NPC476614
0.7206	Intermediate Similarity	NPC142754
0.7206	Intermediate Similarity	NPC296697
0.72	Intermediate Similarity	NPC477372
0.72	Intermediate Similarity	NPC136150
0.7193	Intermediate Similarity	NPC91962
0.7183	Intermediate Similarity	NPC20025
0.7167	Intermediate Similarity	NPC37644
0.7167	Intermediate Similarity	NPC14002
0.7164	Intermediate Similarity	NPC189917
0.7164	Intermediate Similarity	NPC168824
0.7164	Intermediate Similarity	NPC96812
0.7164	Intermediate Similarity	NPC39462
0.7164	Intermediate Similarity	NPC107704
0.7164	Intermediate Similarity	NPC43300
0.7162	Intermediate Similarity	NPC229204
0.7162	Intermediate Similarity	NPC469620
0.7143	Intermediate Similarity	NPC225467
0.7143	Intermediate Similarity	NPC21944
0.7143	Intermediate Similarity	NPC49088
0.7143	Intermediate Similarity	NPC144627
0.7143	Intermediate Similarity	NPC474562
0.7143	Intermediate Similarity	NPC469737
0.7123	Intermediate Similarity	NPC276769
0.7123	Intermediate Similarity	NPC91665
0.7121	Intermediate Similarity	NPC150162
0.7105	Intermediate Similarity	NPC20262
0.7105	Intermediate Similarity	NPC469804
0.7105	Intermediate Similarity	NPC142253
0.7105	Intermediate Similarity	NPC469806
0.7105	Intermediate Similarity	NPC193347
0.7105	Intermediate Similarity	NPC469799
0.7105	Intermediate Similarity	NPC469805
0.7105	Intermediate Similarity	NPC472239
0.7105	Intermediate Similarity	NPC3511
0.7105	Intermediate Similarity	NPC320514
0.7105	Intermediate Similarity	NPC256750
0.7101	Intermediate Similarity	NPC477857
0.7101	Intermediate Similarity	NPC286814
0.7083	Intermediate Similarity	NPC469803

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 NPC94991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	3143
0.2-0.3	4206
0.3-0.4	1059
0.4-0.5	274
0.5-0.6	188
0.6-0.7	71
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
0.8438	Intermediate Similarity	NPD4137	Phase 3
0.8308	Intermediate Similarity	NPD4747	Approved
0.8308	Intermediate Similarity	NPD4691	Approved
0.8182	Intermediate Similarity	NPD5276	Approved
0.8	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD4058	Approved
0.7941	Intermediate Similarity	NPD5733	Approved
0.7941	Intermediate Similarity	NPD4687	Approved
0.7705	Intermediate Similarity	NPD287	Approved
0.7105	Intermediate Similarity	NPD4221	Approved
0.7105	Intermediate Similarity	NPD4223	Phase 3
0.7013	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD3133	Approved
0.6923	Remote Similarity	NPD4197	Approved
0.6923	Remote Similarity	NPD3666	Approved
0.6912	Remote Similarity	NPD7331	Phase 2
0.6835	Remote Similarity	NPD5329	Approved
0.68	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3617	Approved
0.675	Remote Similarity	NPD3618	Phase 1
0.675	Remote Similarity	NPD7521	Approved
0.675	Remote Similarity	NPD4690	Approved
0.675	Remote Similarity	NPD4693	Phase 3
0.675	Remote Similarity	NPD5205	Approved
0.675	Remote Similarity	NPD7146	Approved
0.675	Remote Similarity	NPD4694	Approved
0.675	Remote Similarity	NPD7334	Approved
0.675	Remote Similarity	NPD4688	Approved
0.675	Remote Similarity	NPD4138	Approved
0.675	Remote Similarity	NPD5279	Phase 3
0.675	Remote Similarity	NPD5280	Approved
0.675	Remote Similarity	NPD6409	Approved
0.675	Remote Similarity	NPD4689	Approved
0.675	Remote Similarity	NPD6684	Approved
0.675	Remote Similarity	NPD5690	Phase 2
0.675	Remote Similarity	NPD5330	Approved
0.6724	Remote Similarity	NPD345	Approved
0.6724	Remote Similarity	NPD343	Approved
0.6724	Remote Similarity	NPD344	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6623	Remote Similarity	NPD4695	Discontinued
0.6585	Remote Similarity	NPD6672	Approved
0.6585	Remote Similarity	NPD6903	Approved
0.6585	Remote Similarity	NPD5737	Approved
0.6585	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4518	Approved
0.6585	Remote Similarity	NPD5208	Approved
0.6543	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7341	Phase 2
0.6506	Remote Similarity	NPD6673	Approved
0.6506	Remote Similarity	NPD6904	Approved
0.6506	Remote Similarity	NPD6080	Approved
0.6506	Remote Similarity	NPD4753	Phase 2
0.6506	Remote Similarity	NPD5328	Approved
0.65	Remote Similarity	NPD3668	Phase 3
0.65	Remote Similarity	NPD4786	Approved
0.6429	Remote Similarity	NPD5207	Approved
0.6429	Remote Similarity	NPD4096	Approved
0.6429	Remote Similarity	NPD5692	Phase 3
0.6364	Remote Similarity	NPD5783	Phase 3
0.6353	Remote Similarity	NPD5281	Approved
0.6353	Remote Similarity	NPD6079	Approved
0.6353	Remote Similarity	NPD5694	Approved
0.6353	Remote Similarity	NPD6050	Approved
0.6353	Remote Similarity	NPD5693	Phase 1
0.6353	Remote Similarity	NPD5284	Approved
0.6341	Remote Similarity	NPD4623	Approved
0.6341	Remote Similarity	NPD4519	Discontinued
0.6341	Remote Similarity	NPD6098	Approved
0.6329	Remote Similarity	NPD8028	Phase 2
0.6282	Remote Similarity	NPD4195	Approved
0.6279	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5785	Approved
0.622	Remote Similarity	NPD5363	Approved
0.6207	Remote Similarity	NPD6001	Approved
0.6203	Remote Similarity	NPD5368	Approved
0.6154	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5210	Approved
0.6136	Remote Similarity	NPD4629	Approved
0.6136	Remote Similarity	NPD5695	Phase 3
0.6125	Remote Similarity	NPD5369	Approved
0.6125	Remote Similarity	NPD4692	Approved
0.6125	Remote Similarity	NPD4139	Approved
0.6092	Remote Similarity	NPD5133	Approved
0.6087	Remote Similarity	NPD4191	Approved
0.6087	Remote Similarity	NPD4192	Approved
0.6087	Remote Similarity	NPD4193	Approved
0.6087	Remote Similarity	NPD4194	Approved
0.6071	Remote Similarity	NPD3573	Approved
0.6067	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5222	Approved
0.6067	Remote Similarity	NPD5221	Approved
0.6067	Remote Similarity	NPD4697	Phase 3
0.6049	Remote Similarity	NPD5209	Approved
0.6049	Remote Similarity	NPD4269	Approved
0.6049	Remote Similarity	NPD4270	Approved
0.6049	Remote Similarity	NPD6435	Approved
0.6024	Remote Similarity	NPD1694	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD4252	Approved
0.5976	Remote Similarity	NPD4788	Approved
0.5976	Remote Similarity	NPD5362	Discontinued
0.5972	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD5654	Approved
0.5946	Remote Similarity	NPD6923	Approved
0.5946	Remote Similarity	NPD6922	Approved
0.5934	Remote Similarity	NPD5696	Approved
0.5909	Remote Similarity	NPD6399	Phase 3
0.587	Remote Similarity	NPD4696	Approved
0.587	Remote Similarity	NPD4700	Approved
0.587	Remote Similarity	NPD5285	Approved
0.587	Remote Similarity	NPD5286	Approved
0.5867	Remote Similarity	NPD7143	Approved
0.5867	Remote Similarity	NPD7144	Approved
0.5843	Remote Similarity	NPD5282	Discontinued
0.5824	Remote Similarity	NPD5959	Approved
0.5806	Remote Similarity	NPD5223	Approved
0.5795	Remote Similarity	NPD7515	Phase 2
0.5789	Remote Similarity	NPD7152	Approved
0.5789	Remote Similarity	NPD7150	Approved
0.5789	Remote Similarity	NPD7151	Approved
0.5789	Remote Similarity	NPD4243	Approved
0.5781	Remote Similarity	NPD28	Approved
0.5781	Remote Similarity	NPD29	Approved
0.5769	Remote Similarity	NPD8039	Approved
0.5765	Remote Similarity	NPD5786	Approved
0.5747	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5091	Approved
0.5745	Remote Similarity	NPD4633	Approved
0.5745	Remote Similarity	NPD5224	Approved
0.5745	Remote Similarity	NPD5226	Approved
0.5745	Remote Similarity	NPD5211	Phase 2
0.5745	Remote Similarity	NPD5225	Approved
0.5732	Remote Similarity	NPD857	Phase 3
0.5684	Remote Similarity	NPD5174	Approved
0.5684	Remote Similarity	NPD6052	Approved
0.5684	Remote Similarity	NPD5175	Approved
0.5684	Remote Similarity	NPD4754	Approved
0.5667	Remote Similarity	NPD7748	Approved
0.5667	Remote Similarity	NPD7900	Approved
0.5667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD4784	Approved
0.5641	Remote Similarity	NPD6924	Approved
0.5641	Remote Similarity	NPD4785	Approved
0.5641	Remote Similarity	NPD6926	Approved
0.5625	Remote Similarity	NPD5141	Approved
0.5616	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.561	Remote Similarity	NPD4822	Approved
0.561	Remote Similarity	NPD4819	Approved
0.561	Remote Similarity	NPD4820	Approved
0.561	Remote Similarity	NPD4821	Approved
0.5606	Remote Similarity	NPD3172	Approved
0.5604	Remote Similarity	NPD1698	Clinical (unspecified phase)

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