NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	404.26
Volume:	443.236
LogP:	3.32
LogD:	3.228
LogS:	-4.702
# Rotatable Bonds:	6
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.537
Synthetic Accessibility Score:	4.784
Fsp3:	0.583
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:	-4.735
MDCK Permeability:	5.041098120273091e-05
Pgp-inhibitor:	0.771
Pgp-substrate:	0.223
Human Intestinal Absorption (HIA):	0.989
20% Bioavailability (F20%):	0.609
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	79.32890319824219%
Volume Distribution (VD):	0.744
Pgp-substrate:	14.245035171508789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.091
CYP2C9-substrate:	0.61
CYP2D6-inhibitor:	0.283
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.451
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	3.104
Half-life (T1/2):	0.534

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.668
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.756
Carcinogencity:	0.036
Eye Corrosion:	0.004
Eye Irritation:	0.032
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC477086

Natural Product ID:	NPC477086
*Common Name:**	(1R,2S,3E,7R,8E,11E)-2-Acetoxy-4-(acetoxymethyl)-1-isopropenyl-8,12-dimethylcyclotetradeca-3,8,11-triene-7-ol
IUPAC Name:	[(1E,3S,4R,7E,10E,12R)-3-acetyloxy-12-hydroxy-7,11-dimethyl-4-prop-1-en-2-ylcyclotetradeca-1,7,10-trien-1-yl]methyl acetate
Synonyms:
Standard InCHIKey:	VEMVDCAUWIBDLU-FUHDERAGSA-N
Standard InCHI:	InChI=1S/C24H36O5/c1-16(2)22-12-10-17(3)8-7-9-18(4)23(27)13-11-21(15-28-19(5)25)14-24(22)29-20(6)26/h8-9,14,22-24,27H,1,7,10-13,15H2,2-6H3/b17-8+,18-9+,21-14+/t22-,23-,24+/m1/s1
SMILES:	C/C/1=C\C/C=C(/[C@@H](CC/C(=C\[C@@H]([C@H](CC1)C(=C)C)OC(=O)C)/COC(=O)C)O)\C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44481241
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000008] Cembrane 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
NPO11748	Eunicea knighti	Species	Plexauridae	Eukaryota	n.a.	Santa Marta Bay, Colombian Caribbean	2007-MAY	PMID[19778088]
NPO11748	Eunicea knighti	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
MIC	3
Others	6

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1271	Organism	Bacillus sp.	Bacillus sp.	IZ	=	8	mm	PMID[19778088]
NPT2221	Organism	Ochrobactrum pseudogrignonense	Ochrobactrum pseudogrignonense	IZ	=	8	mm	PMID[19778088]
NPT3980	Organism	Kocuria sp. 10-4DEP	Kocuria sp. 10-4DEP	IZ	=	6	mm	PMID[19778088]
NPT3981	Organism	Oceanobacillus iheyensis	Oceanobacillus iheyensis	IZ	=	6	mm	PMID[19778088]
NPT3982	Organism	Alteromonas sp.	Alteromonas sp.	IZ	=	6	mm	PMID[19778088]
NPT2221	Organism	Ochrobactrum pseudogrignonense	Ochrobactrum pseudogrignonense	IZ	=	6	mm	PMID[19778088]
NPT2221	Organism	Ochrobactrum pseudogrignonense	Ochrobactrum pseudogrignonense	MIC	=	30	ug	PMID[19778088]
NPT1271	Organism	Bacillus sp.	Bacillus sp.	MIC	=	30	ug	PMID[19778088]
NPT2221	Organism	Ochrobactrum pseudogrignonense	Ochrobactrum pseudogrignonense	MIC	>	30	ug	PMID[19778088]

☑ 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 NPC477086 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	170
0.1-0.2	1475
0.2-0.3	5280
0.3-0.4	15187
0.4-0.5	11396
0.5-0.6	5971
0.6-0.7	2714
0.7-0.8	475
0.8-0.85	19
0.85-0.9	5
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477087
0.9851	High Similarity	NPC477085
0.9296	High Similarity	NPC84360
0.9265	High Similarity	NPC4299
0.9118	High Similarity	NPC101622
0.8784	High Similarity	NPC86971
0.8784	High Similarity	NPC477088
0.863	High Similarity	NPC469880
0.8592	High Similarity	NPC477084
0.8592	High Similarity	NPC472254
0.8533	High Similarity	NPC139712
0.8451	Intermediate Similarity	NPC473361
0.8451	Intermediate Similarity	NPC329904
0.8354	Intermediate Similarity	NPC471494
0.8312	Intermediate Similarity	NPC184208
0.8312	Intermediate Similarity	NPC315731
0.8312	Intermediate Similarity	NPC8538
0.831	Intermediate Similarity	NPC269841
0.8267	Intermediate Similarity	NPC477203
0.8228	Intermediate Similarity	NPC160517
0.8228	Intermediate Similarity	NPC78673
0.8228	Intermediate Similarity	NPC186155
0.8169	Intermediate Similarity	NPC305698
0.8148	Intermediate Similarity	NPC313658
0.8148	Intermediate Similarity	NPC471055
0.8148	Intermediate Similarity	NPC471056
0.8148	Intermediate Similarity	NPC316138
0.8133	Intermediate Similarity	NPC477202
0.8082	Intermediate Similarity	NPC316185
0.8077	Intermediate Similarity	NPC112868
0.8052	Intermediate Similarity	NPC321728
0.8052	Intermediate Similarity	NPC471537
0.8052	Intermediate Similarity	NPC226226
0.8052	Intermediate Similarity	NPC55304
0.8028	Intermediate Similarity	NPC259299
0.8026	Intermediate Similarity	NPC320630
0.8026	Intermediate Similarity	NPC116177
0.8026	Intermediate Similarity	NPC7563
0.8025	Intermediate Similarity	NPC311163
0.8025	Intermediate Similarity	NPC186332
0.8025	Intermediate Similarity	NPC47220
0.8025	Intermediate Similarity	NPC61527
0.8	Intermediate Similarity	NPC474776
0.7973	Intermediate Similarity	NPC185186
0.7973	Intermediate Similarity	NPC327383
0.7973	Intermediate Similarity	NPC329890
0.7973	Intermediate Similarity	NPC329914
0.7945	Intermediate Similarity	NPC476012
0.7945	Intermediate Similarity	NPC476037
0.7927	Intermediate Similarity	NPC199382
0.7922	Intermediate Similarity	NPC93763
0.7922	Intermediate Similarity	NPC108816
0.791	Intermediate Similarity	NPC226848
0.7901	Intermediate Similarity	NPC21469
0.7901	Intermediate Similarity	NPC137033
0.7901	Intermediate Similarity	NPC471223
0.7901	Intermediate Similarity	NPC242233
0.7901	Intermediate Similarity	NPC67081
0.7895	Intermediate Similarity	NPC256720
0.7895	Intermediate Similarity	NPC188860
0.7895	Intermediate Similarity	NPC236228
0.7875	Intermediate Similarity	NPC250315
0.7875	Intermediate Similarity	NPC116543
0.7875	Intermediate Similarity	NPC231601
0.7867	Intermediate Similarity	NPC315843
0.7857	Intermediate Similarity	NPC474761
0.7857	Intermediate Similarity	NPC3952
0.7857	Intermediate Similarity	NPC476004
0.7848	Intermediate Similarity	NPC475944
0.7848	Intermediate Similarity	NPC474894
0.7831	Intermediate Similarity	NPC474471
0.7831	Intermediate Similarity	NPC227379
0.7826	Intermediate Similarity	NPC55376
0.7808	Intermediate Similarity	NPC151481
0.7794	Intermediate Similarity	NPC122239
0.7792	Intermediate Similarity	NPC315394
0.7792	Intermediate Similarity	NPC233071
0.7792	Intermediate Similarity	NPC476439
0.7792	Intermediate Similarity	NPC40049
0.7778	Intermediate Similarity	NPC472266
0.7778	Intermediate Similarity	NPC102048
0.7778	Intermediate Similarity	NPC73603
0.7763	Intermediate Similarity	NPC285840
0.7763	Intermediate Similarity	NPC327041
0.7746	Intermediate Similarity	NPC282760
0.7738	Intermediate Similarity	NPC295312
0.7738	Intermediate Similarity	NPC474032
0.7738	Intermediate Similarity	NPC246028
0.7738	Intermediate Similarity	NPC133450
0.7722	Intermediate Similarity	NPC474739
0.7711	Intermediate Similarity	NPC477959
0.7711	Intermediate Similarity	NPC474765
0.7711	Intermediate Similarity	NPC160138
0.7703	Intermediate Similarity	NPC469660
0.7692	Intermediate Similarity	NPC248775
0.7692	Intermediate Similarity	NPC267231
0.7692	Intermediate Similarity	NPC474816
0.7692	Intermediate Similarity	NPC471465
0.7692	Intermediate Similarity	NPC196653
0.7692	Intermediate Similarity	NPC127526
0.7692	Intermediate Similarity	NPC209135
0.7674	Intermediate Similarity	NPC109406
0.7674	Intermediate Similarity	NPC472195
0.7674	Intermediate Similarity	NPC238090
0.7674	Intermediate Similarity	NPC472196
0.7654	Intermediate Similarity	NPC11620
0.7654	Intermediate Similarity	NPC69469
0.7654	Intermediate Similarity	NPC40746
0.7654	Intermediate Similarity	NPC23748
0.7654	Intermediate Similarity	NPC473390
0.7654	Intermediate Similarity	NPC477667
0.7654	Intermediate Similarity	NPC474809
0.7654	Intermediate Similarity	NPC169575
0.7654	Intermediate Similarity	NPC131669
0.7647	Intermediate Similarity	NPC177668
0.7647	Intermediate Similarity	NPC475855
0.7647	Intermediate Similarity	NPC220216
0.7632	Intermediate Similarity	NPC477204
0.7632	Intermediate Similarity	NPC107654
0.7632	Intermediate Similarity	NPC470686
0.7632	Intermediate Similarity	NPC474280
0.7632	Intermediate Similarity	NPC140287
0.7625	Intermediate Similarity	NPC24417
0.7625	Intermediate Similarity	NPC52861
0.7619	Intermediate Similarity	NPC473715
0.7619	Intermediate Similarity	NPC153805
0.7595	Intermediate Similarity	NPC242767
0.7595	Intermediate Similarity	NPC470149
0.7595	Intermediate Similarity	NPC470148
0.7595	Intermediate Similarity	NPC325869
0.7595	Intermediate Similarity	NPC180725
0.759	Intermediate Similarity	NPC164393
0.759	Intermediate Similarity	NPC477668
0.759	Intermediate Similarity	NPC122502
0.7586	Intermediate Similarity	NPC472467
0.7586	Intermediate Similarity	NPC159698
0.7564	Intermediate Similarity	NPC475711
0.7564	Intermediate Similarity	NPC474278
0.7564	Intermediate Similarity	NPC262747
0.7561	Intermediate Similarity	NPC158756
0.7561	Intermediate Similarity	NPC476804
0.7561	Intermediate Similarity	NPC266718
0.7558	Intermediate Similarity	NPC471324
0.7558	Intermediate Similarity	NPC473321
0.7558	Intermediate Similarity	NPC234335
0.7558	Intermediate Similarity	NPC114172
0.7558	Intermediate Similarity	NPC206679
0.7558	Intermediate Similarity	NPC30515
0.7558	Intermediate Similarity	NPC476084
0.7558	Intermediate Similarity	NPC124374
0.7558	Intermediate Similarity	NPC476075
0.7534	Intermediate Similarity	NPC473357
0.7534	Intermediate Similarity	NPC193029
0.7531	Intermediate Similarity	NPC471298
0.7531	Intermediate Similarity	NPC229825
0.7531	Intermediate Similarity	NPC123908
0.7531	Intermediate Similarity	NPC10080
0.7529	Intermediate Similarity	NPC261320
0.75	Intermediate Similarity	NPC470147
0.75	Intermediate Similarity	NPC133226
0.75	Intermediate Similarity	NPC86005
0.75	Intermediate Similarity	NPC469802
0.75	Intermediate Similarity	NPC248602
0.75	Intermediate Similarity	NPC36954
0.75	Intermediate Similarity	NPC316629
0.7471	Intermediate Similarity	NPC99653
0.7471	Intermediate Similarity	NPC475838
0.7471	Intermediate Similarity	NPC476049
0.7471	Intermediate Similarity	NPC159092
0.7471	Intermediate Similarity	NPC228451
0.7471	Intermediate Similarity	NPC125674
0.7471	Intermediate Similarity	NPC475912
0.747	Intermediate Similarity	NPC35933
0.747	Intermediate Similarity	NPC11804
0.747	Intermediate Similarity	NPC470755
0.747	Intermediate Similarity	NPC255307
0.7468	Intermediate Similarity	NPC3852
0.7465	Intermediate Similarity	NPC29697
0.7465	Intermediate Similarity	NPC473508
0.7442	Intermediate Similarity	NPC144133
0.7442	Intermediate Similarity	NPC313670
0.7442	Intermediate Similarity	NPC473448
0.7442	Intermediate Similarity	NPC473619
0.7442	Intermediate Similarity	NPC209816
0.7442	Intermediate Similarity	NPC316228
0.7442	Intermediate Similarity	NPC179394
0.7442	Intermediate Similarity	NPC51004
0.7439	Intermediate Similarity	NPC161045
0.7439	Intermediate Similarity	NPC52923
0.7439	Intermediate Similarity	NPC49208
0.7439	Intermediate Similarity	NPC472473
0.7439	Intermediate Similarity	NPC44261
0.7439	Intermediate Similarity	NPC471297
0.7436	Intermediate Similarity	NPC271070
0.7436	Intermediate Similarity	NPC301525
0.7436	Intermediate Similarity	NPC68819
0.7432	Intermediate Similarity	NPC272961
0.7429	Intermediate Similarity	NPC19241
0.7416	Intermediate Similarity	NPC476315
0.7416	Intermediate Similarity	NPC472995

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 NPC477086 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1951
0.2-0.3	3784
0.3-0.4	2354
0.4-0.5	696
0.5-0.6	160
0.6-0.7	53
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
0.7647	Intermediate Similarity	NPD46	Approved
0.7647	Intermediate Similarity	NPD7838	Discovery
0.7647	Intermediate Similarity	NPD6698	Approved
0.75	Intermediate Similarity	NPD4250	Approved
0.75	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4251	Approved
0.7439	Intermediate Similarity	NPD7154	Phase 3
0.7381	Intermediate Similarity	NPD4249	Approved
0.7356	Intermediate Similarity	NPD7983	Approved
0.7262	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4268	Approved
0.725	Intermediate Similarity	NPD4271	Approved
0.7229	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5344	Discontinued
0.7079	Intermediate Similarity	NPD5778	Approved
0.7079	Intermediate Similarity	NPD5779	Approved
0.7073	Intermediate Similarity	NPD4822	Approved
0.7073	Intermediate Similarity	NPD4821	Approved
0.7073	Intermediate Similarity	NPD4820	Approved
0.7073	Intermediate Similarity	NPD4819	Approved
0.7067	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5332	Approved
0.7024	Intermediate Similarity	NPD5331	Approved
0.6989	Remote Similarity	NPD7640	Approved
0.6989	Remote Similarity	NPD7639	Approved
0.6988	Remote Similarity	NPD4790	Discontinued
0.6966	Remote Similarity	NPD7637	Suspended
0.6944	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4269	Approved
0.6905	Remote Similarity	NPD4270	Approved
0.6882	Remote Similarity	NPD7638	Approved
0.6867	Remote Similarity	NPD4252	Approved
0.6854	Remote Similarity	NPD5785	Approved
0.6848	Remote Similarity	NPD7839	Suspended
0.6829	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6648	Approved
0.6782	Remote Similarity	NPD5786	Approved
0.6714	Remote Similarity	NPD342	Phase 1
0.6667	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5363	Approved
0.6628	Remote Similarity	NPD6695	Phase 3
0.6628	Remote Similarity	NPD6110	Phase 1
0.6622	Remote Similarity	NPD368	Approved
0.6618	Remote Similarity	NPD6927	Phase 3
0.6588	Remote Similarity	NPD5369	Approved
0.6556	Remote Similarity	NPD5370	Suspended
0.6552	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6371	Approved
0.6526	Remote Similarity	NPD4225	Approved
0.6512	Remote Similarity	NPD6435	Approved
0.6477	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD8039	Approved
0.6447	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4732	Discontinued
0.6413	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD4265	Approved
0.6353	Remote Similarity	NPD6929	Approved
0.6337	Remote Similarity	NPD6686	Approved
0.6333	Remote Similarity	NPD7524	Approved
0.6333	Remote Similarity	NPD7750	Discontinued
0.6327	Remote Similarity	NPD7632	Discontinued
0.6322	Remote Similarity	NPD5209	Approved
0.631	Remote Similarity	NPD6925	Approved
0.631	Remote Similarity	NPD5776	Phase 2
0.6279	Remote Similarity	NPD5368	Approved
0.6279	Remote Similarity	NPD7332	Phase 2
0.6279	Remote Similarity	NPD6931	Approved
0.6279	Remote Similarity	NPD7514	Phase 3
0.6279	Remote Similarity	NPD6930	Phase 2
0.6265	Remote Similarity	NPD8264	Approved
0.625	Remote Similarity	NPD6053	Discontinued
0.6237	Remote Similarity	NPD6411	Approved
0.6235	Remote Similarity	NPD7145	Approved
0.6234	Remote Similarity	NPD3197	Phase 1
0.6222	Remote Similarity	NPD6422	Discontinued
0.6211	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6902	Approved
0.6196	Remote Similarity	NPD1695	Approved
0.6196	Remote Similarity	NPD6051	Approved
0.6136	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4756	Discovery
0.6064	Remote Similarity	NPD7087	Discontinued
0.6058	Remote Similarity	NPD6421	Discontinued
0.6047	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6898	Phase 1
0.6	Remote Similarity	NPD6109	Phase 1
0.6	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6399	Phase 3
0.5952	Remote Similarity	NPD6924	Approved
0.5952	Remote Similarity	NPD6926	Approved
0.5946	Remote Similarity	NPD8513	Phase 3
0.5946	Remote Similarity	NPD8516	Approved
0.5946	Remote Similarity	NPD8517	Approved
0.5946	Remote Similarity	NPD8515	Approved
0.5941	Remote Similarity	NPD6647	Phase 2
0.5934	Remote Similarity	NPD6893	Approved
0.593	Remote Similarity	NPD6932	Approved
0.589	Remote Similarity	NPD4266	Approved
0.589	Remote Similarity	NPD3194	Approved
0.589	Remote Similarity	NPD3196	Approved
0.589	Remote Similarity	NPD3195	Phase 2
0.5854	Remote Similarity	NPD6923	Approved
0.5854	Remote Similarity	NPD6922	Approved
0.5825	Remote Similarity	NPD4211	Phase 1
0.5825	Remote Similarity	NPD6640	Phase 3
0.5824	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7328	Approved
0.5818	Remote Similarity	NPD7327	Approved
0.5814	Remote Similarity	NPD6933	Approved
0.5806	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD8033	Approved
0.5795	Remote Similarity	NPD6683	Phase 2
0.5783	Remote Similarity	NPD7143	Approved
0.5783	Remote Similarity	NPD7144	Approved
0.5773	Remote Similarity	NPD5282	Discontinued
0.5773	Remote Similarity	NPD7748	Approved
0.5769	Remote Similarity	NPD4191	Approved
0.5769	Remote Similarity	NPD4194	Approved
0.5769	Remote Similarity	NPD4193	Approved
0.5769	Remote Similarity	NPD4192	Approved
0.5766	Remote Similarity	NPD7516	Approved
0.5761	Remote Similarity	NPD1694	Approved
0.5753	Remote Similarity	NPD3172	Approved
0.5739	Remote Similarity	NPD8273	Phase 1
0.5729	Remote Similarity	NPD7515	Phase 2
0.5727	Remote Similarity	NPD7115	Discovery
0.5727	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD5343	Approved
0.5714	Remote Similarity	NPD7152	Approved
0.5714	Remote Similarity	NPD8377	Approved
0.5714	Remote Similarity	NPD7151	Approved
0.5714	Remote Similarity	NPD7150	Approved
0.5714	Remote Similarity	NPD8294	Approved
0.5698	Remote Similarity	NPD6942	Approved
0.5698	Remote Similarity	NPD7339	Approved
0.569	Remote Similarity	NPD8074	Phase 3
0.5679	Remote Similarity	NPD7331	Phase 2
0.5673	Remote Similarity	NPD5048	Discontinued
0.567	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8335	Approved
0.5664	Remote Similarity	NPD8378	Approved
0.5664	Remote Similarity	NPD8444	Approved
0.5664	Remote Similarity	NPD8379	Approved
0.5664	Remote Similarity	NPD8380	Approved
0.5664	Remote Similarity	NPD8296	Approved
0.5664	Remote Similarity	NPD7503	Approved
0.566	Remote Similarity	NPD6413	Approved
0.566	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4228	Discovery
0.5652	Remote Similarity	NPD39	Approved
0.5652	Remote Similarity	NPD4786	Approved
0.5634	Remote Similarity	NPD4220	Pre-registration
0.5634	Remote Similarity	NPD3173	Approved
0.5632	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7136	Phase 2
0.5625	Remote Similarity	NPD3168	Discontinued
0.5619	Remote Similarity	NPD6685	Approved
0.5618	Remote Similarity	NPD7645	Phase 2
0.5604	Remote Similarity	NPD3667	Approved
0.56	Remote Similarity	NPD6083	Phase 2
0.56	Remote Similarity	NPD6084	Phase 2
0.56	Remote Similarity	NPD7902	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