NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.18
Volume:	254.401
LogP:	4.055
LogD:	3.941
LogS:	-3.881
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.653
Synthetic Accessibility Score:	4.563
Fsp3:	0.8
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:	-4.44
MDCK Permeability:	2.244346796942409e-05
Pgp-inhibitor:	0.389
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.474
Plasma Protein Binding (PPB):	85.82310485839844%
Volume Distribution (VD):	0.684
Pgp-substrate:	12.69700813293457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.745
CYP1A2-substrate:	0.245
CYP2C19-inhibitor:	0.546
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.178
CYP2D6-substrate:	0.216
CYP3A4-inhibitor:	0.641
CYP3A4-substrate:	0.362

ADMET: Excretion

Clearance (CL):	16.247
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.456
Drug-inuced Liver Injury (DILI):	0.355
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.431
Skin Sensitization:	0.948
Carcinogencity:	0.829
Eye Corrosion:	0.847
Eye Irritation:	0.908
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC165695

Natural Product ID:	NPC165695
*Common Name:**	(-)-Acorenone
IUPAC Name:	(1S,4S,5S)-1,8-dimethyl-4-propan-2-ylspiro[4.5]dec-7-en-9-one
Synonyms:	(-)-Acorenone
Standard InCHIKey:	HBTHUBMUAHAWBC-YDHLFZDLSA-N
Standard InCHI:	InChI=1S/C15H24O/c1-10(2)13-6-5-12(4)15(13)8-7-11(3)14(16)9-15/h7,10,12-13H,5-6,8-9H2,1-4H3/t12-,13-,15-/m0/s1
SMILES:	CC(C)[C@@H]1CC[C@H](C)[C@]21CC=C(C)C(=O)C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1814555
PubChem CID:	12480741
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20476749]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21563811]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[21936523]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22671987]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22951040]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23373216]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23713285]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[26296476]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26305406]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[29116780]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8666	Acorus tatarinowii	Species	Acoraceae	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
EC50	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Emax	=	241.0	%	PMID[522984]
NPT2	Others	Unspecified		EC50	=	34000.0	nM	PMID[522984]

☑ 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 NPC165695 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	188
0.1-0.2	2764
0.2-0.3	15605
0.3-0.4	12365
0.4-0.5	7140
0.5-0.6	3482
0.6-0.7	946
0.7-0.8	158
0.8-0.85	29
0.85-0.9	11
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9322	High Similarity	NPC25853
0.918	High Similarity	NPC212210
0.9167	High Similarity	NPC213152
0.9016	High Similarity	NPC32285
0.8983	High Similarity	NPC266295
0.8983	High Similarity	NPC30215
0.8983	High Similarity	NPC94991
0.8833	High Similarity	NPC259261
0.8814	High Similarity	NPC55004
0.8814	High Similarity	NPC267626
0.8814	High Similarity	NPC49575
0.875	High Similarity	NPC475523
0.8657	High Similarity	NPC303613
0.8657	High Similarity	NPC474228
0.8657	High Similarity	NPC470045
0.8657	High Similarity	NPC251705
0.8657	High Similarity	NPC470044
0.8636	High Similarity	NPC159577
0.8636	High Similarity	NPC282593
0.8636	High Similarity	NPC307176
0.8636	High Similarity	NPC35734
0.8636	High Similarity	NPC265782
0.8636	High Similarity	NPC251929
0.8636	High Similarity	NPC2634
0.8571	High Similarity	NPC473902
0.8548	High Similarity	NPC475795
0.8507	High Similarity	NPC234707
0.8507	High Similarity	NPC115023
0.8507	High Similarity	NPC5701
0.8507	High Similarity	NPC54123
0.85	High Similarity	NPC230823
0.85	High Similarity	NPC115385
0.8485	Intermediate Similarity	NPC139397
0.8448	Intermediate Similarity	NPC268564
0.8438	Intermediate Similarity	NPC251118
0.8413	Intermediate Similarity	NPC472306
0.8406	Intermediate Similarity	NPC293803
0.8387	Intermediate Similarity	NPC127582
0.8361	Intermediate Similarity	NPC27610
0.8361	Intermediate Similarity	NPC56905
0.8358	Intermediate Similarity	NPC260040
0.8333	Intermediate Similarity	NPC20610
0.8286	Intermediate Similarity	NPC69408
0.8281	Intermediate Similarity	NPC475124
0.8281	Intermediate Similarity	NPC285371
0.8281	Intermediate Similarity	NPC6697
0.8261	Intermediate Similarity	NPC255021
0.8261	Intermediate Similarity	NPC309852
0.8254	Intermediate Similarity	NPC97322
0.8235	Intermediate Similarity	NPC304983
0.8235	Intermediate Similarity	NPC305501
0.8226	Intermediate Similarity	NPC285594
0.8226	Intermediate Similarity	NPC276764
0.8226	Intermediate Similarity	NPC96551
0.8226	Intermediate Similarity	NPC143834
0.8226	Intermediate Similarity	NPC472304
0.8209	Intermediate Similarity	NPC182815
0.8209	Intermediate Similarity	NPC61702
0.8209	Intermediate Similarity	NPC162867
0.8209	Intermediate Similarity	NPC256846
0.8154	Intermediate Similarity	NPC470329
0.8125	Intermediate Similarity	NPC288253
0.8125	Intermediate Similarity	NPC167256
0.8095	Intermediate Similarity	NPC270042
0.8065	Intermediate Similarity	NPC311852
0.8065	Intermediate Similarity	NPC170799
0.8065	Intermediate Similarity	NPC308108
0.806	Intermediate Similarity	NPC260474
0.806	Intermediate Similarity	NPC310992
0.806	Intermediate Similarity	NPC87141
0.806	Intermediate Similarity	NPC188292
0.8033	Intermediate Similarity	NPC20603
0.803	Intermediate Similarity	NPC92327
0.803	Intermediate Similarity	NPC323005
0.803	Intermediate Similarity	NPC176171
0.8	Intermediate Similarity	NPC474796
0.8	Intermediate Similarity	NPC474797
0.8	Intermediate Similarity	NPC329866
0.7971	Intermediate Similarity	NPC181204
0.7971	Intermediate Similarity	NPC470078
0.7945	Intermediate Similarity	NPC90965
0.7945	Intermediate Similarity	NPC170793
0.7931	Intermediate Similarity	NPC176819
0.7931	Intermediate Similarity	NPC32351
0.7931	Intermediate Similarity	NPC163984
0.7931	Intermediate Similarity	NPC58970
0.791	Intermediate Similarity	NPC176107
0.7887	Intermediate Similarity	NPC255650
0.7838	Intermediate Similarity	NPC474509
0.7833	Intermediate Similarity	NPC474141
0.7833	Intermediate Similarity	NPC23117
0.7833	Intermediate Similarity	NPC296311
0.7826	Intermediate Similarity	NPC246722
0.7826	Intermediate Similarity	NPC151045
0.7826	Intermediate Similarity	NPC214770
0.7826	Intermediate Similarity	NPC477856
0.7808	Intermediate Similarity	NPC228911
0.7797	Intermediate Similarity	NPC64866
0.7794	Intermediate Similarity	NPC155198
0.7778	Intermediate Similarity	NPC469793
0.7778	Intermediate Similarity	NPC469796
0.7727	Intermediate Similarity	NPC469662
0.7714	Intermediate Similarity	NPC223187
0.7714	Intermediate Similarity	NPC474562
0.7705	Intermediate Similarity	NPC5626
0.7692	Intermediate Similarity	NPC60565
0.7647	Intermediate Similarity	NPC4370
0.7647	Intermediate Similarity	NPC290350
0.7639	Intermediate Similarity	NPC251435
0.7639	Intermediate Similarity	NPC473171
0.7632	Intermediate Similarity	NPC142253
0.7632	Intermediate Similarity	NPC3511
0.7632	Intermediate Similarity	NPC472239
0.7627	Intermediate Similarity	NPC228776
0.7627	Intermediate Similarity	NPC116906
0.7619	Intermediate Similarity	NPC192427
0.7619	Intermediate Similarity	NPC193695
0.7586	Intermediate Similarity	NPC91962
0.7581	Intermediate Similarity	NPC275472
0.7581	Intermediate Similarity	NPC200258
0.7576	Intermediate Similarity	NPC202118
0.7576	Intermediate Similarity	NPC197238
0.7571	Intermediate Similarity	NPC40574
0.7568	Intermediate Similarity	NPC469996
0.7541	Intermediate Similarity	NPC37644
0.7541	Intermediate Similarity	NPC14002
0.7536	Intermediate Similarity	NPC469688
0.75	Intermediate Similarity	NPC236623
0.75	Intermediate Similarity	NPC477372
0.75	Intermediate Similarity	NPC27438
0.7465	Intermediate Similarity	NPC190035
0.7465	Intermediate Similarity	NPC225467
0.7463	Intermediate Similarity	NPC150162
0.746	Intermediate Similarity	NPC473733
0.7458	Intermediate Similarity	NPC145311
0.7436	Intermediate Similarity	NPC87552
0.7436	Intermediate Similarity	NPC7927
0.7436	Intermediate Similarity	NPC230527
0.7429	Intermediate Similarity	NPC469677
0.7429	Intermediate Similarity	NPC477857
0.7419	Intermediate Similarity	NPC100809
0.7419	Intermediate Similarity	NPC63396
0.7419	Intermediate Similarity	NPC209431
0.7419	Intermediate Similarity	NPC202850
0.7403	Intermediate Similarity	NPC320514
0.7403	Intermediate Similarity	NPC472867
0.7403	Intermediate Similarity	NPC193347
0.7397	Intermediate Similarity	NPC77501
0.7397	Intermediate Similarity	NPC476346
0.7377	Intermediate Similarity	NPC471751
0.7368	Intermediate Similarity	NPC45495
0.7368	Intermediate Similarity	NPC472478
0.7361	Intermediate Similarity	NPC56747
0.7361	Intermediate Similarity	NPC109576
0.7361	Intermediate Similarity	NPC130016
0.7361	Intermediate Similarity	NPC180015
0.7353	Intermediate Similarity	NPC183422
0.7342	Intermediate Similarity	NPC29447
0.7342	Intermediate Similarity	NPC8571
0.7333	Intermediate Similarity	NPC82635
0.7333	Intermediate Similarity	NPC470052
0.7308	Intermediate Similarity	NPC41539
0.7297	Intermediate Similarity	NPC474463
0.7297	Intermediate Similarity	NPC215481
0.7297	Intermediate Similarity	NPC1254
0.7286	Intermediate Similarity	NPC469679
0.7286	Intermediate Similarity	NPC39157
0.7286	Intermediate Similarity	NPC82477
0.7286	Intermediate Similarity	NPC296697
0.7286	Intermediate Similarity	NPC142754
0.726	Intermediate Similarity	NPC469691
0.726	Intermediate Similarity	NPC167049
0.7258	Intermediate Similarity	NPC45283
0.7258	Intermediate Similarity	NPC69898
0.7258	Intermediate Similarity	NPC295777
0.7246	Intermediate Similarity	NPC43300
0.7246	Intermediate Similarity	NPC39462
0.7246	Intermediate Similarity	NPC96812
0.7246	Intermediate Similarity	NPC107704
0.7246	Intermediate Similarity	NPC189917
0.7246	Intermediate Similarity	NPC168824
0.7237	Intermediate Similarity	NPC472490
0.7237	Intermediate Similarity	NPC477371
0.7237	Intermediate Similarity	NPC7232
0.7231	Intermediate Similarity	NPC60772
0.7222	Intermediate Similarity	NPC144627
0.7222	Intermediate Similarity	NPC21944
0.7215	Intermediate Similarity	NPC16287
0.7215	Intermediate Similarity	NPC237712
0.7215	Intermediate Similarity	NPC181743
0.7215	Intermediate Similarity	NPC178025
0.7215	Intermediate Similarity	NPC214043
0.7215	Intermediate Similarity	NPC144258
0.7215	Intermediate Similarity	NPC85774
0.7215	Intermediate Similarity	NPC473246
0.7206	Intermediate Similarity	NPC4638
0.72	Intermediate Similarity	NPC91665
0.7183	Intermediate Similarity	NPC286814
0.7179	Intermediate Similarity	NPC469806
0.7179	Intermediate Similarity	NPC100297

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 NPC165695 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	3003
0.2-0.3	4284
0.3-0.4	1135
0.4-0.5	266
0.5-0.6	198
0.6-0.7	71
0.7-0.8	9
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD4747	Approved
0.8636	High Similarity	NPD4691	Approved
0.8485	Intermediate Similarity	NPD4137	Phase 3
0.8261	Intermediate Similarity	NPD4058	Approved
0.8261	Intermediate Similarity	NPD5733	Approved
0.8261	Intermediate Similarity	NPD4687	Approved
0.8235	Intermediate Similarity	NPD5276	Approved
0.8065	Intermediate Similarity	NPD287	Approved
0.806	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4223	Phase 3
0.7403	Intermediate Similarity	NPD4221	Approved
0.7308	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5690	Phase 2
0.7215	Intermediate Similarity	NPD4197	Approved
0.7125	Intermediate Similarity	NPD5329	Approved
0.7037	Intermediate Similarity	NPD4693	Phase 3
0.7037	Intermediate Similarity	NPD4694	Approved
0.7037	Intermediate Similarity	NPD4689	Approved
0.7037	Intermediate Similarity	NPD5280	Approved
0.7037	Intermediate Similarity	NPD4690	Approved
0.7037	Intermediate Similarity	NPD4688	Approved
0.7037	Intermediate Similarity	NPD5205	Approved
0.7037	Intermediate Similarity	NPD4138	Approved
0.7	Intermediate Similarity	NPD3665	Phase 1
0.7	Intermediate Similarity	NPD3666	Approved
0.7	Intermediate Similarity	NPD3133	Approved
0.6883	Remote Similarity	NPD3617	Approved
0.6867	Remote Similarity	NPD5208	Approved
0.6867	Remote Similarity	NPD5737	Approved
0.6867	Remote Similarity	NPD6672	Approved
0.6833	Remote Similarity	NPD343	Approved
0.6833	Remote Similarity	NPD345	Approved
0.6833	Remote Similarity	NPD344	Approved
0.6829	Remote Similarity	NPD7521	Approved
0.6829	Remote Similarity	NPD6409	Approved
0.6829	Remote Similarity	NPD6684	Approved
0.6829	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7334	Approved
0.6829	Remote Similarity	NPD3618	Phase 1
0.6829	Remote Similarity	NPD7146	Approved
0.6829	Remote Similarity	NPD5330	Approved
0.6829	Remote Similarity	NPD5279	Phase 3
0.6824	Remote Similarity	NPD6079	Approved
0.6795	Remote Similarity	NPD4195	Approved
0.679	Remote Similarity	NPD4786	Approved
0.6786	Remote Similarity	NPD5328	Approved
0.6786	Remote Similarity	NPD4753	Phase 2
0.6786	Remote Similarity	NPD6673	Approved
0.6786	Remote Similarity	NPD6080	Approved
0.6786	Remote Similarity	NPD6904	Approved
0.6761	Remote Similarity	NPD7331	Phase 2
0.675	Remote Similarity	NPD3667	Approved
0.6709	Remote Similarity	NPD4695	Discontinued
0.6706	Remote Similarity	NPD5692	Phase 3
0.6706	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6628	Remote Similarity	NPD5281	Approved
0.6628	Remote Similarity	NPD5284	Approved
0.6628	Remote Similarity	NPD5694	Approved
0.6628	Remote Similarity	NPD6050	Approved
0.6628	Remote Similarity	NPD5693	Phase 1
0.6627	Remote Similarity	NPD6098	Approved
0.6625	Remote Similarity	NPD8028	Phase 2
0.6591	Remote Similarity	NPD4629	Approved
0.6591	Remote Similarity	NPD5210	Approved
0.6585	Remote Similarity	NPD3668	Phase 3
0.6552	Remote Similarity	NPD4202	Approved
0.6517	Remote Similarity	NPD5221	Approved
0.6517	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5222	Approved
0.6512	Remote Similarity	NPD4096	Approved
0.6506	Remote Similarity	NPD1694	Approved
0.6477	Remote Similarity	NPD6001	Approved
0.6456	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5173	Approved
0.6429	Remote Similarity	NPD4519	Discontinued
0.6429	Remote Similarity	NPD4623	Approved
0.642	Remote Similarity	NPD4692	Approved
0.642	Remote Similarity	NPD4139	Approved
0.6404	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5695	Phase 3
0.6389	Remote Similarity	NPD7341	Phase 2
0.6364	Remote Similarity	NPD5133	Approved
0.6353	Remote Similarity	NPD3573	Approved
0.6333	Remote Similarity	NPD4697	Phase 3
0.6304	Remote Similarity	NPD5286	Approved
0.6304	Remote Similarity	NPD5285	Approved
0.6304	Remote Similarity	NPD4696	Approved
0.6265	Remote Similarity	NPD4788	Approved
0.6264	Remote Similarity	NPD4755	Approved
0.6264	Remote Similarity	NPD6083	Phase 2
0.6264	Remote Similarity	NPD6084	Phase 2
0.6237	Remote Similarity	NPD5223	Approved
0.6222	Remote Similarity	NPD5654	Approved
0.6196	Remote Similarity	NPD5696	Approved
0.618	Remote Similarity	NPD6399	Phase 3
0.617	Remote Similarity	NPD5211	Phase 2
0.617	Remote Similarity	NPD5225	Approved
0.617	Remote Similarity	NPD4633	Approved
0.617	Remote Similarity	NPD5224	Approved
0.617	Remote Similarity	NPD5226	Approved
0.617	Remote Similarity	NPD5091	Approved
0.6145	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4700	Approved
0.6111	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5175	Approved
0.6105	Remote Similarity	NPD5174	Approved
0.6104	Remote Similarity	NPD4243	Approved
0.6087	Remote Similarity	NPD5959	Approved
0.6081	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5141	Approved
0.6029	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD4192	Approved
0.5972	Remote Similarity	NPD4194	Approved
0.5972	Remote Similarity	NPD4193	Approved
0.5972	Remote Similarity	NPD4191	Approved
0.5957	Remote Similarity	NPD6404	Discontinued
0.5955	Remote Similarity	NPD5785	Approved
0.5949	Remote Similarity	NPD4784	Approved
0.5949	Remote Similarity	NPD4785	Approved
0.5938	Remote Similarity	NPD6052	Approved
0.5938	Remote Similarity	NPD4754	Approved
0.593	Remote Similarity	NPD1696	Phase 3
0.593	Remote Similarity	NPD5363	Approved
0.5918	Remote Similarity	NPD5697	Approved
0.5918	Remote Similarity	NPD6614	Approved
0.5904	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD7515	Phase 2
0.5875	Remote Similarity	NPD5275	Approved
0.5875	Remote Similarity	NPD6942	Approved
0.5875	Remote Similarity	NPD7339	Approved
0.5875	Remote Similarity	NPD4190	Phase 3
0.5862	Remote Similarity	NPD319	Phase 1
0.5859	Remote Similarity	NPD4729	Approved
0.5859	Remote Similarity	NPD5168	Approved
0.5859	Remote Similarity	NPD6881	Approved
0.5859	Remote Similarity	NPD5128	Approved
0.5859	Remote Similarity	NPD6899	Approved
0.5859	Remote Similarity	NPD4730	Approved
0.5859	Remote Similarity	NPD6011	Approved
0.5844	Remote Similarity	NPD6922	Approved
0.5844	Remote Similarity	NPD6923	Approved
0.5843	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD6675	Approved
0.5816	Remote Similarity	NPD6008	Approved
0.5816	Remote Similarity	NPD4768	Approved
0.5816	Remote Similarity	NPD7128	Approved
0.5816	Remote Similarity	NPD4767	Approved
0.5816	Remote Similarity	NPD5739	Approved
0.5816	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD6012	Approved
0.58	Remote Similarity	NPD6014	Approved
0.58	Remote Similarity	NPD6013	Approved
0.5769	Remote Similarity	NPD7143	Approved
0.5769	Remote Similarity	NPD7144	Approved
0.5765	Remote Similarity	NPD5209	Approved
0.5761	Remote Similarity	NPD7900	Approved
0.5761	Remote Similarity	NPD7748	Approved
0.5761	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5701	Approved
0.5745	Remote Similarity	NPD3495	Discontinued
0.5743	Remote Similarity	NPD7290	Approved
0.5743	Remote Similarity	NPD5169	Approved
0.5743	Remote Similarity	NPD4634	Approved
0.5743	Remote Similarity	NPD7102	Approved
0.5743	Remote Similarity	NPD5250	Approved
0.5743	Remote Similarity	NPD5247	Approved
0.5743	Remote Similarity	NPD5251	Approved
0.5743	Remote Similarity	NPD5135	Approved
0.5743	Remote Similarity	NPD5248	Approved
0.5743	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5249	Phase 3
0.5743	Remote Similarity	NPD6883	Approved
0.5714	Remote Similarity	NPD5368	Approved
0.57	Remote Similarity	NPD7320	Approved
0.5698	Remote Similarity	NPD5362	Discontinued
0.5696	Remote Similarity	NPD7150	Approved
0.5696	Remote Similarity	NPD7152	Approved
0.5696	Remote Similarity	NPD7151	Approved
0.5686	Remote Similarity	NPD6847	Approved
0.5686	Remote Similarity	NPD5216	Approved
0.5686	Remote Similarity	NPD6650	Approved
0.5686	Remote Similarity	NPD5127	Approved
0.5686	Remote Similarity	NPD5215	Approved
0.5686	Remote Similarity	NPD6649	Approved
0.5686	Remote Similarity	NPD5217	Approved
0.5686	Remote Similarity	NPD8130	Phase 1
0.5686	Remote Similarity	NPD6617	Approved
0.5686	Remote Similarity	NPD6869	Approved
0.5679	Remote Similarity	NPD8039	Approved
0.5667	Remote Similarity	NPD5783	Phase 3
0.5652	Remote Similarity	NPD1508	Approved
0.5652	Remote Similarity	NPD7631	Approved
0.5647	Remote Similarity	NPD5369	Approved
0.5647	Remote Similarity	NPD857	Phase 3
0.5645	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6373	Approved
0.5644	Remote Similarity	NPD6372	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