NPASS Compound

Structure

CID176171 OpenBabel06191715552D 22 25 0 0 1 0 0 0 0 0999 V2000 -4.7134 -3.1371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7353 -2.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0140 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4263 -0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 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 1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4263 -1.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9563 -0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4752 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4752 -1.6691 0.0000 C 0 0 1 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 2.9344 -0.6237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 2 14 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 18 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 1 0 0 0 16 22 2 0 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 1 0 0 0 19 21 1 1 0 0 0 20 3 1 1 0 0 0 21 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.21
Volume:	335.791
LogP:	4.619
LogD:	4.414
LogS:	-5.019
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	4.988
Fsp3:	0.667
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:	-4.716
MDCK Permeability:	2.8062035198672675e-05
Pgp-inhibitor:	0.876
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	97.83248901367188%
Volume Distribution (VD):	1.716
Pgp-substrate:	3.293529510498047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.892
CYP1A2-substrate:	0.591
CYP2C19-inhibitor:	0.744
CYP2C19-substrate:	0.769
CYP2C9-inhibitor:	0.499
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.889
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.69

ADMET: Excretion

Clearance (CL):	3.582
Half-life (T1/2):	0.279

ADMET: Toxicity

hERG Blockers:	0.283
Human Hepatotoxicity (H-HT):	0.611
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.785
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.97
Carcinogencity:	0.471
Eye Corrosion:	0.962
Eye Irritation:	0.722
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC176171

Natural Product ID:	NPC176171
*Common Name:**	Carijodienone
IUPAC Name:	(3R,3aR,5aS,6R,8aS,8bS)-3-ethenyl-3',3a-dimethylspiro[1,2,3,4,5,5a,7,8,8a,8b-decahydro-as-indacene-6,4'-cyclohexa-2,5-diene]-1'-one
Synonyms:	Carijodienone
Standard InCHIKey:	WBURTZSEYTVSRX-OPJRWSFGSA-N
Standard InCHI:	InChI=1S/C21H28O/c1-4-15-5-6-18-17-8-12-21(11-7-16(22)13-14(21)2)19(17)9-10-20(15,18)3/h4,7,11,13,15,17-19H,1,5-6,8-10,12H2,2-3H3/t15-,17-,18-,19-,20+,21+/m0/s1
SMILES:	C=C[C@H]1CC[C@H]2[C@@H]3CC[C@@]4(C=CC(=O)C=C4C)[C@H]3CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689217
PubChem CID:	51042413
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

*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
NPO30138	Carijoa	Genus	Clavulariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21235217]

☑ 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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	6.0	ug.mL-1	PMID[455226]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	5.0	ug.mL-1	PMID[455226]

☑ 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 NPC176171 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	176
0.1-0.2	2414
0.2-0.3	17283
0.3-0.4	10258
0.4-0.5	7927
0.5-0.6	3746
0.6-0.7	804
0.7-0.8	81
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9365	High Similarity	NPC92327
0.9219	High Similarity	NPC176107
0.8551	High Similarity	NPC470045
0.8551	High Similarity	NPC251705
0.8551	High Similarity	NPC470044
0.8548	High Similarity	NPC60772
0.8406	Intermediate Similarity	NPC54123
0.8406	Intermediate Similarity	NPC234707
0.8406	Intermediate Similarity	NPC115023
0.831	Intermediate Similarity	NPC293803
0.8286	Intermediate Similarity	NPC474228
0.8286	Intermediate Similarity	NPC303613
0.8261	Intermediate Similarity	NPC35734
0.8261	Intermediate Similarity	NPC2634
0.8261	Intermediate Similarity	NPC265782
0.8261	Intermediate Similarity	NPC307176
0.8261	Intermediate Similarity	NPC251929
0.8261	Intermediate Similarity	NPC282593
0.8261	Intermediate Similarity	NPC159577
0.8197	Intermediate Similarity	NPC5626
0.8194	Intermediate Similarity	NPC474463
0.8194	Intermediate Similarity	NPC69408
0.8169	Intermediate Similarity	NPC309852
0.8143	Intermediate Similarity	NPC305501
0.8143	Intermediate Similarity	NPC5701
0.8116	Intermediate Similarity	NPC182815
0.8116	Intermediate Similarity	NPC139397
0.8033	Intermediate Similarity	NPC14002
0.803	Intermediate Similarity	NPC165695
0.8	Intermediate Similarity	NPC260040
0.7973	Intermediate Similarity	NPC105197
0.7971	Intermediate Similarity	NPC260474
0.7971	Intermediate Similarity	NPC20610
0.7971	Intermediate Similarity	NPC188292
0.7941	Intermediate Similarity	NPC323005
0.7917	Intermediate Similarity	NPC255021
0.7917	Intermediate Similarity	NPC329866
0.7917	Intermediate Similarity	NPC474796
0.7917	Intermediate Similarity	NPC474797
0.791	Intermediate Similarity	NPC212210
0.7887	Intermediate Similarity	NPC470078
0.7879	Intermediate Similarity	NPC213152
0.7867	Intermediate Similarity	NPC190211
0.7857	Intermediate Similarity	NPC256846
0.7808	Intermediate Similarity	NPC255650
0.7794	Intermediate Similarity	NPC251118
0.7763	Intermediate Similarity	NPC474509
0.7761	Intermediate Similarity	NPC472306
0.7742	Intermediate Similarity	NPC23117
0.7733	Intermediate Similarity	NPC228911
0.7727	Intermediate Similarity	NPC25853
0.7727	Intermediate Similarity	NPC127582
0.7727	Intermediate Similarity	NPC270042
0.7714	Intermediate Similarity	NPC87141
0.7714	Intermediate Similarity	NPC310992
0.7703	Intermediate Similarity	NPC469793
0.7703	Intermediate Similarity	NPC469796
0.7647	Intermediate Similarity	NPC475124
0.7647	Intermediate Similarity	NPC285371
0.7647	Intermediate Similarity	NPC469662
0.7632	Intermediate Similarity	NPC90965
0.7632	Intermediate Similarity	NPC170793
0.7576	Intermediate Similarity	NPC472304
0.7576	Intermediate Similarity	NPC276764
0.7571	Intermediate Similarity	NPC475523
0.7568	Intermediate Similarity	NPC473171
0.7541	Intermediate Similarity	NPC200129
0.75	Intermediate Similarity	NPC202118
0.75	Intermediate Similarity	NPC477856
0.75	Intermediate Similarity	NPC197238
0.75	Intermediate Similarity	NPC288253
0.75	Intermediate Similarity	NPC214770
0.75	Intermediate Similarity	NPC40574
0.7465	Intermediate Similarity	NPC155198
0.746	Intermediate Similarity	NPC295777
0.746	Intermediate Similarity	NPC69898
0.7436	Intermediate Similarity	NPC6434
0.7424	Intermediate Similarity	NPC311852
0.7424	Intermediate Similarity	NPC266295
0.7424	Intermediate Similarity	NPC56905
0.7424	Intermediate Similarity	NPC469769
0.7424	Intermediate Similarity	NPC94991
0.7424	Intermediate Similarity	NPC27610
0.7424	Intermediate Similarity	NPC30215
0.7397	Intermediate Similarity	NPC225467
0.7397	Intermediate Similarity	NPC223187
0.7397	Intermediate Similarity	NPC181204
0.7375	Intermediate Similarity	NPC33913
0.7342	Intermediate Similarity	NPC472239
0.7342	Intermediate Similarity	NPC142253
0.7342	Intermediate Similarity	NPC3511
0.7333	Intermediate Similarity	NPC476346
0.7313	Intermediate Similarity	NPC259261
0.7284	Intermediate Similarity	NPC29447
0.7273	Intermediate Similarity	NPC267626
0.7273	Intermediate Similarity	NPC49575
0.7273	Intermediate Similarity	NPC55004
0.7273	Intermediate Similarity	NPC469996
0.7273	Intermediate Similarity	NPC82635
0.7273	Intermediate Similarity	NPC470052
0.7273	Intermediate Similarity	NPC115385
0.726	Intermediate Similarity	NPC475728
0.7246	Intermediate Similarity	NPC32285
0.7237	Intermediate Similarity	NPC1254
0.7231	Intermediate Similarity	NPC123194
0.7215	Intermediate Similarity	NPC477372
0.7183	Intermediate Similarity	NPC259156
0.7183	Intermediate Similarity	NPC242945
0.7164	Intermediate Similarity	NPC308108
0.7164	Intermediate Similarity	NPC170799
0.7162	Intermediate Similarity	NPC304983
0.7162	Intermediate Similarity	NPC474562
0.7162	Intermediate Similarity	NPC190035
0.716	Intermediate Similarity	NPC87552
0.716	Intermediate Similarity	NPC472265
0.7143	Intermediate Similarity	NPC91665
0.7143	Intermediate Similarity	NPC52449
0.7143	Intermediate Similarity	NPC169275
0.7143	Intermediate Similarity	NPC473902
0.7143	Intermediate Similarity	NPC6697
0.7125	Intermediate Similarity	NPC469799
0.7125	Intermediate Similarity	NPC100297
0.7125	Intermediate Similarity	NPC469805
0.7125	Intermediate Similarity	NPC469806
0.7125	Intermediate Similarity	NPC472867
0.7125	Intermediate Similarity	NPC193347
0.7125	Intermediate Similarity	NPC320514
0.7125	Intermediate Similarity	NPC469804
0.7123	Intermediate Similarity	NPC477857
0.7108	Intermediate Similarity	NPC93778
0.7101	Intermediate Similarity	NPC469728
0.7101	Intermediate Similarity	NPC475795
0.7101	Intermediate Similarity	NPC60565
0.7097	Intermediate Similarity	NPC17518
0.7089	Intermediate Similarity	NPC472478
0.7089	Intermediate Similarity	NPC469798
0.7089	Intermediate Similarity	NPC469797
0.7083	Intermediate Similarity	NPC290350
0.7083	Intermediate Similarity	NPC4370
0.7073	Intermediate Similarity	NPC8571
0.7067	Intermediate Similarity	NPC130016
0.7067	Intermediate Similarity	NPC109576
0.7067	Intermediate Similarity	NPC52667
0.7067	Intermediate Similarity	NPC56747
0.7067	Intermediate Similarity	NPC180015
0.7037	Intermediate Similarity	NPC474976
0.7037	Intermediate Similarity	NPC474790
0.7037	Intermediate Similarity	NPC279639
0.7037	Intermediate Similarity	NPC41539
0.7037	Intermediate Similarity	NPC3856
0.7027	Intermediate Similarity	NPC246722
0.7027	Intermediate Similarity	NPC151045
0.7015	Intermediate Similarity	NPC208749
0.7015	Intermediate Similarity	NPC230823
0.7015	Intermediate Similarity	NPC22019
0.7015	Intermediate Similarity	NPC281986
0.7015	Intermediate Similarity	NPC321568
0.6988	Remote Similarity	NPC222613
0.6988	Remote Similarity	NPC118648
0.6988	Remote Similarity	NPC475022
0.6986	Remote Similarity	NPC39157
0.6986	Remote Similarity	NPC82477
0.6986	Remote Similarity	NPC142754
0.6986	Remote Similarity	NPC296697
0.6974	Remote Similarity	NPC22134
0.697	Remote Similarity	NPC200258
0.6962	Remote Similarity	NPC472490
0.6962	Remote Similarity	NPC477371
0.6951	Remote Similarity	NPC178025
0.6951	Remote Similarity	NPC237712
0.6951	Remote Similarity	NPC181743
0.6951	Remote Similarity	NPC85774
0.6951	Remote Similarity	NPC16287
0.6951	Remote Similarity	NPC473246
0.6951	Remote Similarity	NPC214043
0.6951	Remote Similarity	NPC144258
0.6944	Remote Similarity	NPC96812
0.6944	Remote Similarity	NPC39462
0.6944	Remote Similarity	NPC189917
0.6944	Remote Similarity	NPC107704
0.6944	Remote Similarity	NPC255781
0.6944	Remote Similarity	NPC168824
0.6944	Remote Similarity	NPC43300
0.6941	Remote Similarity	NPC262043
0.6941	Remote Similarity	NPC177141
0.6935	Remote Similarity	NPC124851
0.6933	Remote Similarity	NPC5734
0.6923	Remote Similarity	NPC268564
0.6923	Remote Similarity	NPC470557
0.6914	Remote Similarity	NPC327969
0.6914	Remote Similarity	NPC321289
0.6905	Remote Similarity	NPC476293
0.6905	Remote Similarity	NPC58063
0.6905	Remote Similarity	NPC136548
0.6901	Remote Similarity	NPC4638
0.6892	Remote Similarity	NPC286814
0.6885	Remote Similarity	NPC86683
0.6883	Remote Similarity	NPC65650
0.6875	Remote Similarity	NPC476809
0.6867	Remote Similarity	NPC472940

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 NPC176171 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2523
0.2-0.3	4820
0.3-0.4	1131
0.4-0.5	229
0.5-0.6	184
0.6-0.7	82
0.7-0.8	11
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
0.8261	Intermediate Similarity	NPD4691	Approved
0.8261	Intermediate Similarity	NPD4747	Approved
0.8169	Intermediate Similarity	NPD4058	Approved
0.8169	Intermediate Similarity	NPD4687	Approved
0.8116	Intermediate Similarity	NPD4137	Phase 3
0.7917	Intermediate Similarity	NPD5733	Approved
0.7887	Intermediate Similarity	NPD5276	Approved
0.7867	Intermediate Similarity	NPD4195	Approved
0.7714	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5690	Phase 2
0.7164	Intermediate Similarity	NPD287	Approved
0.7125	Intermediate Similarity	NPD4223	Phase 3
0.7125	Intermediate Similarity	NPD4221	Approved
0.6974	Remote Similarity	NPD4784	Approved
0.6974	Remote Similarity	NPD4785	Approved
0.6951	Remote Similarity	NPD4197	Approved
0.6933	Remote Similarity	NPD4243	Approved
0.6867	Remote Similarity	NPD5329	Approved
0.686	Remote Similarity	NPD5207	Approved
0.6824	Remote Similarity	NPD6903	Approved
0.6786	Remote Similarity	NPD4694	Approved
0.6786	Remote Similarity	NPD4688	Approved
0.6786	Remote Similarity	NPD4689	Approved
0.6786	Remote Similarity	NPD5280	Approved
0.6786	Remote Similarity	NPD4693	Phase 3
0.6786	Remote Similarity	NPD4138	Approved
0.6786	Remote Similarity	NPD4690	Approved
0.6786	Remote Similarity	NPD5205	Approved
0.6782	Remote Similarity	NPD6079	Approved
0.6747	Remote Similarity	NPD3665	Phase 1
0.6747	Remote Similarity	NPD3133	Approved
0.6747	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD4190	Phase 3
0.6667	Remote Similarity	NPD5275	Approved
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6628	Remote Similarity	NPD6672	Approved
0.6628	Remote Similarity	NPD5208	Approved
0.6628	Remote Similarity	NPD5737	Approved
0.6625	Remote Similarity	NPD3617	Approved
0.6591	Remote Similarity	NPD5281	Approved
0.6591	Remote Similarity	NPD5694	Approved
0.6591	Remote Similarity	NPD5284	Approved
0.6588	Remote Similarity	NPD5279	Phase 3
0.6588	Remote Similarity	NPD3618	Phase 1
0.6588	Remote Similarity	NPD7521	Approved
0.6588	Remote Similarity	NPD7334	Approved
0.6588	Remote Similarity	NPD6409	Approved
0.6588	Remote Similarity	NPD6684	Approved
0.6588	Remote Similarity	NPD5330	Approved
0.6588	Remote Similarity	NPD7146	Approved
0.6588	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7144	Approved
0.6579	Remote Similarity	NPD7143	Approved
0.6556	Remote Similarity	NPD5210	Approved
0.6556	Remote Similarity	NPD4629	Approved
0.6552	Remote Similarity	NPD4753	Phase 2
0.6552	Remote Similarity	NPD5328	Approved
0.6552	Remote Similarity	NPD6904	Approved
0.6552	Remote Similarity	NPD6673	Approved
0.6552	Remote Similarity	NPD6080	Approved
0.6548	Remote Similarity	NPD4786	Approved
0.6506	Remote Similarity	NPD3667	Approved
0.6494	Remote Similarity	NPD7151	Approved
0.6494	Remote Similarity	NPD7150	Approved
0.6494	Remote Similarity	NPD7152	Approved
0.6484	Remote Similarity	NPD5222	Approved
0.6484	Remote Similarity	NPD5221	Approved
0.6484	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5692	Phase 3
0.6463	Remote Similarity	NPD4695	Discontinued
0.6447	Remote Similarity	NPD6923	Approved
0.6447	Remote Similarity	NPD6922	Approved
0.6444	Remote Similarity	NPD6001	Approved
0.6437	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5173	Approved
0.6404	Remote Similarity	NPD5693	Phase 1
0.6404	Remote Similarity	NPD6050	Approved
0.6395	Remote Similarity	NPD4623	Approved
0.6395	Remote Similarity	NPD4519	Discontinued
0.6395	Remote Similarity	NPD6098	Approved
0.6393	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4194	Approved
0.6389	Remote Similarity	NPD4191	Approved
0.6389	Remote Similarity	NPD4193	Approved
0.6389	Remote Similarity	NPD4192	Approved
0.6386	Remote Similarity	NPD8028	Phase 2
0.6375	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6939	Phase 2
0.6353	Remote Similarity	NPD3668	Phase 3
0.6333	Remote Similarity	NPD4202	Approved
0.6322	Remote Similarity	NPD3573	Approved
0.6292	Remote Similarity	NPD4096	Approved
0.6277	Remote Similarity	NPD5286	Approved
0.6277	Remote Similarity	NPD5285	Approved
0.6277	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD4518	Approved
0.6211	Remote Similarity	NPD5223	Approved
0.6196	Remote Similarity	NPD5695	Phase 3
0.619	Remote Similarity	NPD4139	Approved
0.619	Remote Similarity	NPD4692	Approved
0.617	Remote Similarity	NPD5290	Discontinued
0.6154	Remote Similarity	NPD5133	Approved
0.6146	Remote Similarity	NPD5225	Approved
0.6146	Remote Similarity	NPD5224	Approved
0.6146	Remote Similarity	NPD5226	Approved
0.6146	Remote Similarity	NPD4633	Approved
0.6146	Remote Similarity	NPD5211	Phase 2
0.6146	Remote Similarity	NPD5091	Approved
0.6129	Remote Similarity	NPD4697	Phase 3
0.6125	Remote Similarity	NPD6924	Approved
0.6125	Remote Similarity	NPD6926	Approved
0.6098	Remote Similarity	NPD6932	Approved
0.6082	Remote Similarity	NPD5175	Approved
0.6082	Remote Similarity	NPD5174	Approved
0.6071	Remote Similarity	NPD7525	Registered
0.6064	Remote Similarity	NPD4755	Approved
0.6064	Remote Similarity	NPD6084	Phase 2
0.6064	Remote Similarity	NPD6083	Phase 2
0.6061	Remote Similarity	NPD8262	Approved
0.6047	Remote Similarity	NPD4788	Approved
0.6024	Remote Similarity	NPD7145	Approved
0.6022	Remote Similarity	NPD5654	Approved
0.602	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD6051	Approved
0.5978	Remote Similarity	NPD6399	Phase 3
0.5976	Remote Similarity	NPD6933	Approved
0.5938	Remote Similarity	NPD4700	Approved
0.593	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6052	Approved
0.5915	Remote Similarity	NPD4219	Approved
0.5909	Remote Similarity	NPD1694	Approved
0.5904	Remote Similarity	NPD5776	Phase 2
0.5904	Remote Similarity	NPD6925	Approved
0.59	Remote Similarity	NPD5697	Approved
0.59	Remote Similarity	NPD6614	Approved
0.5895	Remote Similarity	NPD5959	Approved
0.5882	Remote Similarity	NPD7514	Phase 3
0.5842	Remote Similarity	NPD4729	Approved
0.5842	Remote Similarity	NPD5168	Approved
0.5842	Remote Similarity	NPD6899	Approved
0.5842	Remote Similarity	NPD6881	Approved
0.5842	Remote Similarity	NPD4730	Approved
0.5842	Remote Similarity	NPD7320	Approved
0.5842	Remote Similarity	NPD6011	Approved
0.5833	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6902	Approved
0.58	Remote Similarity	NPD6008	Approved
0.5789	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6014	Approved
0.5784	Remote Similarity	NPD6013	Approved
0.5784	Remote Similarity	NPD6012	Approved
0.5778	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD6404	Discontinued
0.5765	Remote Similarity	NPD6683	Phase 2
0.5765	Remote Similarity	NPD6929	Approved
0.5758	Remote Similarity	NPD345	Approved
0.5758	Remote Similarity	NPD343	Approved
0.5758	Remote Similarity	NPD344	Approved
0.5758	Remote Similarity	NPD4754	Approved
0.5745	Remote Similarity	NPD5707	Approved
0.5729	Remote Similarity	NPD3495	Discontinued
0.5728	Remote Similarity	NPD7102	Approved
0.5728	Remote Similarity	NPD5251	Approved
0.5728	Remote Similarity	NPD5250	Approved
0.5728	Remote Similarity	NPD5247	Approved
0.5728	Remote Similarity	NPD5169	Approved
0.5728	Remote Similarity	NPD5135	Approved
0.5728	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5249	Phase 3
0.5728	Remote Similarity	NPD7290	Approved
0.5728	Remote Similarity	NPD6883	Approved
0.5728	Remote Similarity	NPD4634	Approved
0.5728	Remote Similarity	NPD5248	Approved
0.5714	Remote Similarity	NPD4722	Approved
0.5714	Remote Similarity	NPD4723	Approved
0.5699	Remote Similarity	NPD7515	Phase 2
0.5698	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD7332	Phase 2
0.5698	Remote Similarity	NPD6931	Approved
0.5698	Remote Similarity	NPD4748	Discontinued
0.5698	Remote Similarity	NPD6930	Phase 2
0.5686	Remote Similarity	NPD5128	Approved
0.5673	Remote Similarity	NPD5215	Approved
0.5673	Remote Similarity	NPD6847	Approved
0.5673	Remote Similarity	NPD6869	Approved
0.5673	Remote Similarity	NPD5216	Approved
0.5673	Remote Similarity	NPD5127	Approved
0.5673	Remote Similarity	NPD5217	Approved
0.5673	Remote Similarity	NPD6650	Approved
0.5673	Remote Similarity	NPD6617	Approved
0.5673	Remote Similarity	NPD6649	Approved
0.5673	Remote Similarity	NPD8130	Phase 1
0.5663	Remote Similarity	NPD8264	Approved
0.5652	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD5784	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