NPASS Compound

Structure

NPC276769 OpenBabel07101718312D 22 23 0 0 1 0 0 0 0 0999 V2000 0.1974 -1.7208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3915 -1.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6263 -2.0690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1062 2.9561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9733 0.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4855 0.3844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1138 -0.5440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2962 1.3663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3004 -1.1716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4344 -0.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 1.9987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1538 1.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3980 -0.9174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2992 -1.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6062 2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9761 0.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6343 2.3258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5082 0.8612 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 1.0712 1.2127 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5868 3.3247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5037 0.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 22 1 1 0 0 0 19 13 1 6 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	344.398
LogP:	3.639
LogD:	3.73
LogS:	-4.433
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.567
Synthetic Accessibility Score:	4.974
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.62
MDCK Permeability:	3.123519127257168e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.469
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.87
Plasma Protein Binding (PPB):	87.40422821044922%
Volume Distribution (VD):	0.973
Pgp-substrate:	14.417442321777344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.17
CYP2C19-inhibitor:	0.422
CYP2C19-substrate:	0.759
CYP2C9-inhibitor:	0.466
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.386

ADMET: Excretion

Clearance (CL):	11.146
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.764
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.45
Carcinogencity:	0.863
Eye Corrosion:	0.023
Eye Irritation:	0.02
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC276769

Natural Product ID:	NPC276769
*Common Name:**	(1S,12R)-Dolabella-4(16),7,10-Trien-13S-Ol-3-One
IUPAC Name:	(1S,2S,3aS,9E,12Z)-2-hydroxy-3a,10-dimethyl-6-methylidene-1-propan-2-yl-2,3,4,7,8,11-hexahydro-1H-cyclopenta[11]annulen-5-one
Synonyms:
Standard InCHIKey:	NKHTWDHIBRDYEV-MDTDKSHQSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13(2)19-16-10-9-14(3)7-6-8-15(4)17(21)11-20(16,5)12-18(19)22/h7,10,13,18-19,22H,4,6,8-9,11-12H2,1-3,5H3/b14-7+,16-10-/t18-,19-,20+/m0/s1
SMILES:	C/C/1=CCCC(=C)C(=O)C[C@]2(/C(=CC1)/[C@H](C(C)C)[C@H](C2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472094
PubChem CID:	16091540
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
NPO27081.1	Clavularia inflata	Under-species	n.a.	n.a.	n.a.	formosan soft coral	n.a.	PMID[17067152]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.5	ug ml-1	PMID[515080]

☑ 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 NPC276769 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	167
0.1-0.2	1280
0.2-0.3	6837
0.3-0.4	15611
0.4-0.5	8174
0.5-0.6	6630
0.6-0.7	3390
0.7-0.8	576
0.8-0.85	27
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.88	High Similarity	NPC469646
0.875	High Similarity	NPC10758
0.875	High Similarity	NPC250928
0.8519	High Similarity	NPC36350
0.8462	Intermediate Similarity	NPC261125
0.8462	Intermediate Similarity	NPC181195
0.8452	Intermediate Similarity	NPC477711
0.8434	Intermediate Similarity	NPC477710
0.8421	Intermediate Similarity	NPC474011
0.8421	Intermediate Similarity	NPC251435
0.8333	Intermediate Similarity	NPC474056
0.8272	Intermediate Similarity	NPC476082
0.8272	Intermediate Similarity	NPC278648
0.8256	Intermediate Similarity	NPC125180
0.8171	Intermediate Similarity	NPC230527
0.8171	Intermediate Similarity	NPC7927
0.8158	Intermediate Similarity	NPC300940
0.8125	Intermediate Similarity	NPC164218
0.8125	Intermediate Similarity	NPC472478
0.8101	Intermediate Similarity	NPC475994
0.8072	Intermediate Similarity	NPC202868
0.8049	Intermediate Similarity	NPC62214
0.8046	Intermediate Similarity	NPC109414
0.8026	Intermediate Similarity	NPC469737
0.8025	Intermediate Similarity	NPC136150
0.8	Intermediate Similarity	NPC472490
0.7976	Intermediate Similarity	NPC183736
0.7975	Intermediate Similarity	NPC211279
0.7952	Intermediate Similarity	NPC82902
0.7952	Intermediate Similarity	NPC475796
0.7952	Intermediate Similarity	NPC161423
0.7952	Intermediate Similarity	NPC329043
0.7952	Intermediate Similarity	NPC227064
0.7952	Intermediate Similarity	NPC58841
0.7952	Intermediate Similarity	NPC321187
0.7949	Intermediate Similarity	NPC77501
0.7949	Intermediate Similarity	NPC472256
0.7945	Intermediate Similarity	NPC474329
0.7945	Intermediate Similarity	NPC474304
0.7927	Intermediate Similarity	NPC133844
0.7907	Intermediate Similarity	NPC41217
0.7907	Intermediate Similarity	NPC123912
0.7907	Intermediate Similarity	NPC170775
0.7907	Intermediate Similarity	NPC477943
0.7907	Intermediate Similarity	NPC232747
0.7889	Intermediate Similarity	NPC87090
0.7865	Intermediate Similarity	NPC472932
0.7857	Intermediate Similarity	NPC469948
0.7857	Intermediate Similarity	NPC474218
0.7857	Intermediate Similarity	NPC474853
0.7857	Intermediate Similarity	NPC179006
0.7848	Intermediate Similarity	NPC215481
0.7848	Intermediate Similarity	NPC470525
0.7848	Intermediate Similarity	NPC226242
0.7841	Intermediate Similarity	NPC250575
0.7816	Intermediate Similarity	NPC2946
0.7802	Intermediate Similarity	NPC197386
0.7802	Intermediate Similarity	NPC222011
0.7791	Intermediate Similarity	NPC474854
0.7791	Intermediate Similarity	NPC328313
0.7791	Intermediate Similarity	NPC328539
0.7778	Intermediate Similarity	NPC7232
0.7778	Intermediate Similarity	NPC164308
0.7778	Intermediate Similarity	NPC229204
0.7765	Intermediate Similarity	NPC31564
0.7765	Intermediate Similarity	NPC475022
0.7765	Intermediate Similarity	NPC474778
0.7765	Intermediate Similarity	NPC474733
0.7765	Intermediate Similarity	NPC118648
0.7765	Intermediate Similarity	NPC327115
0.7765	Intermediate Similarity	NPC222613
0.7765	Intermediate Similarity	NPC145879
0.7765	Intermediate Similarity	NPC474732
0.7765	Intermediate Similarity	NPC20688
0.7765	Intermediate Similarity	NPC469994
0.7763	Intermediate Similarity	NPC469677
0.7753	Intermediate Similarity	NPC298919
0.775	Intermediate Similarity	NPC86917
0.7738	Intermediate Similarity	NPC59453
0.7738	Intermediate Similarity	NPC221758
0.7738	Intermediate Similarity	NPC85774
0.7738	Intermediate Similarity	NPC473246
0.7738	Intermediate Similarity	NPC214043
0.7722	Intermediate Similarity	NPC114236
0.7722	Intermediate Similarity	NPC216791
0.7711	Intermediate Similarity	NPC151519
0.7703	Intermediate Similarity	NPC477009
0.7703	Intermediate Similarity	NPC238352
0.7701	Intermediate Similarity	NPC86319
0.7701	Intermediate Similarity	NPC275740
0.7701	Intermediate Similarity	NPC76879
0.7701	Intermediate Similarity	NPC186688
0.7692	Intermediate Similarity	NPC92909
0.7692	Intermediate Similarity	NPC69385
0.7692	Intermediate Similarity	NPC275098
0.7692	Intermediate Similarity	NPC107783
0.7683	Intermediate Similarity	NPC30675
0.7683	Intermediate Similarity	NPC45495
0.7674	Intermediate Similarity	NPC58063
0.7674	Intermediate Similarity	NPC475740
0.7674	Intermediate Similarity	NPC317590
0.7654	Intermediate Similarity	NPC62336
0.7654	Intermediate Similarity	NPC321180
0.764	Intermediate Similarity	NPC206810
0.7634	Intermediate Similarity	NPC477356
0.7632	Intermediate Similarity	NPC469688
0.7625	Intermediate Similarity	NPC242722
0.7619	Intermediate Similarity	NPC118800
0.7619	Intermediate Similarity	NPC472498
0.7619	Intermediate Similarity	NPC474748
0.7619	Intermediate Similarity	NPC470165
0.7614	Intermediate Similarity	NPC69622
0.7609	Intermediate Similarity	NPC147954
0.7609	Intermediate Similarity	NPC477355
0.7606	Intermediate Similarity	NPC30215
0.76	Intermediate Similarity	NPC197089
0.7595	Intermediate Similarity	NPC469691
0.7595	Intermediate Similarity	NPC167049
0.7586	Intermediate Similarity	NPC131470
0.7586	Intermediate Similarity	NPC471722
0.7586	Intermediate Similarity	NPC53911
0.7586	Intermediate Similarity	NPC471941
0.7586	Intermediate Similarity	NPC143767
0.7561	Intermediate Similarity	NPC471890
0.7561	Intermediate Similarity	NPC469690
0.7561	Intermediate Similarity	NPC84185
0.7561	Intermediate Similarity	NPC66677
0.7561	Intermediate Similarity	NPC136033
0.7558	Intermediate Similarity	NPC232156
0.7558	Intermediate Similarity	NPC51014
0.7556	Intermediate Similarity	NPC90453
0.7553	Intermediate Similarity	NPC87351
0.7553	Intermediate Similarity	NPC473424
0.7553	Intermediate Similarity	NPC118405
0.7534	Intermediate Similarity	NPC260573
0.7534	Intermediate Similarity	NPC475795
0.7532	Intermediate Similarity	NPC469914
0.7531	Intermediate Similarity	NPC106078
0.7531	Intermediate Similarity	NPC197659
0.7529	Intermediate Similarity	NPC472265
0.7529	Intermediate Similarity	NPC146683
0.7529	Intermediate Similarity	NPC237712
0.7528	Intermediate Similarity	NPC185936
0.7528	Intermediate Similarity	NPC168027
0.7528	Intermediate Similarity	NPC221282
0.7527	Intermediate Similarity	NPC144956
0.7527	Intermediate Similarity	NPC474720
0.75	Intermediate Similarity	NPC476388
0.75	Intermediate Similarity	NPC472477
0.75	Intermediate Similarity	NPC1015
0.75	Intermediate Similarity	NPC469669
0.75	Intermediate Similarity	NPC96962
0.75	Intermediate Similarity	NPC190554
0.75	Intermediate Similarity	NPC26959
0.75	Intermediate Similarity	NPC119416
0.75	Intermediate Similarity	NPC268406
0.75	Intermediate Similarity	NPC310010
0.75	Intermediate Similarity	NPC472971
0.75	Intermediate Similarity	NPC469678
0.75	Intermediate Similarity	NPC475771
0.75	Intermediate Similarity	NPC326627
0.75	Intermediate Similarity	NPC472475
0.75	Intermediate Similarity	NPC477215
0.75	Intermediate Similarity	NPC97032
0.75	Intermediate Similarity	NPC31985
0.75	Intermediate Similarity	NPC472970
0.75	Intermediate Similarity	NPC7414
0.75	Intermediate Similarity	NPC474885
0.75	Intermediate Similarity	NPC18509
0.75	Intermediate Similarity	NPC2983
0.75	Intermediate Similarity	NPC193347
0.7474	Intermediate Similarity	NPC111323
0.7474	Intermediate Similarity	NPC311612
0.7473	Intermediate Similarity	NPC469599
0.7471	Intermediate Similarity	NPC136548
0.7471	Intermediate Similarity	NPC472481
0.7471	Intermediate Similarity	NPC472324
0.7471	Intermediate Similarity	NPC312215
0.7471	Intermediate Similarity	NPC174619
0.7471	Intermediate Similarity	NPC472484
0.7471	Intermediate Similarity	NPC93778
0.7471	Intermediate Similarity	NPC472482
0.747	Intermediate Similarity	NPC164999
0.747	Intermediate Similarity	NPC2482
0.7444	Intermediate Similarity	NPC202824
0.7444	Intermediate Similarity	NPC472930
0.7444	Intermediate Similarity	NPC37816
0.7444	Intermediate Similarity	NPC472942
0.7444	Intermediate Similarity	NPC477361
0.7444	Intermediate Similarity	NPC474736
0.7444	Intermediate Similarity	NPC69454
0.7444	Intermediate Similarity	NPC25750
0.7442	Intermediate Similarity	NPC471224
0.7442	Intermediate Similarity	NPC474083
0.7442	Intermediate Similarity	NPC470574
0.7442	Intermediate Similarity	NPC102292
0.7442	Intermediate Similarity	NPC476426
0.7439	Intermediate Similarity	NPC192006
0.7436	Intermediate Similarity	NPC318766
0.7419	Intermediate Similarity	NPC166745

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 NPC276769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1936
0.2-0.3	4231
0.3-0.4	1961
0.4-0.5	452
0.5-0.6	181
0.6-0.7	185
0.7-0.8	46
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
0.7952	Intermediate Similarity	NPD3665	Phase 1
0.7952	Intermediate Similarity	NPD3666	Approved
0.7952	Intermediate Similarity	NPD3133	Approved
0.7901	Intermediate Similarity	NPD5368	Approved
0.7738	Intermediate Similarity	NPD4786	Approved
0.7727	Intermediate Similarity	NPD6079	Approved
0.7711	Intermediate Similarity	NPD6435	Approved
0.7711	Intermediate Similarity	NPD3667	Approved
0.7701	Intermediate Similarity	NPD5328	Approved
0.7654	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5363	Approved
0.7619	Intermediate Similarity	NPD5362	Discontinued
0.7614	Intermediate Similarity	NPD5785	Approved
0.759	Intermediate Similarity	NPD5369	Approved
0.7558	Intermediate Similarity	NPD5786	Approved
0.7558	Intermediate Similarity	NPD5279	Phase 3
0.7527	Intermediate Similarity	NPD5286	Approved
0.7527	Intermediate Similarity	NPD4696	Approved
0.7527	Intermediate Similarity	NPD5285	Approved
0.75	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD4269	Approved
0.75	Intermediate Similarity	NPD4270	Approved
0.75	Intermediate Similarity	NPD4221	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD4223	Phase 3
0.7447	Intermediate Similarity	NPD5223	Approved
0.7444	Intermediate Similarity	NPD4202	Approved
0.7412	Intermediate Similarity	NPD4788	Approved
0.7391	Intermediate Similarity	NPD5221	Approved
0.7391	Intermediate Similarity	NPD5222	Approved
0.7391	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5224	Approved
0.7368	Intermediate Similarity	NPD5211	Phase 2
0.7368	Intermediate Similarity	NPD7331	Phase 2
0.7368	Intermediate Similarity	NPD5225	Approved
0.7368	Intermediate Similarity	NPD4633	Approved
0.7368	Intermediate Similarity	NPD5226	Approved
0.7356	Intermediate Similarity	NPD5690	Phase 2
0.7356	Intermediate Similarity	NPD3618	Phase 1
0.734	Intermediate Similarity	NPD4700	Approved
0.7326	Intermediate Similarity	NPD4197	Approved
0.7312	Intermediate Similarity	NPD5173	Approved
0.7292	Intermediate Similarity	NPD5175	Approved
0.7292	Intermediate Similarity	NPD5174	Approved
0.7283	Intermediate Similarity	NPD5210	Approved
0.7283	Intermediate Similarity	NPD4629	Approved
0.7262	Intermediate Similarity	NPD4252	Approved
0.7241	Intermediate Similarity	NPD5329	Approved
0.7216	Intermediate Similarity	NPD5141	Approved
0.7209	Intermediate Similarity	NPD5331	Approved
0.7209	Intermediate Similarity	NPD5332	Approved
0.7204	Intermediate Similarity	NPD4697	Phase 3
0.7191	Intermediate Similarity	NPD4518	Approved
0.7176	Intermediate Similarity	NPD4790	Discontinued
0.7159	Intermediate Similarity	NPD4694	Approved
0.7159	Intermediate Similarity	NPD5280	Approved
0.7159	Intermediate Similarity	NPD4693	Phase 3
0.7159	Intermediate Similarity	NPD4690	Approved
0.7159	Intermediate Similarity	NPD4138	Approved
0.7159	Intermediate Similarity	NPD5205	Approved
0.7159	Intermediate Similarity	NPD4688	Approved
0.7159	Intermediate Similarity	NPD4689	Approved
0.7113	Intermediate Similarity	NPD4754	Approved
0.7097	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5697	Approved
0.7059	Intermediate Similarity	NPD4819	Approved
0.7059	Intermediate Similarity	NPD4695	Discontinued
0.7059	Intermediate Similarity	NPD4822	Approved
0.7059	Intermediate Similarity	NPD4821	Approved
0.7059	Intermediate Similarity	NPD4820	Approved
0.7024	Intermediate Similarity	NPD4268	Approved
0.7024	Intermediate Similarity	NPD4271	Approved
0.7013	Intermediate Similarity	NPD7341	Phase 2
0.7	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD5128	Approved
0.7	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD4729	Approved
0.7	Intermediate Similarity	NPD4730	Approved
0.7	Intermediate Similarity	NPD6881	Approved
0.6988	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6402	Approved
0.697	Remote Similarity	NPD5739	Approved
0.697	Remote Similarity	NPD4768	Approved
0.697	Remote Similarity	NPD7128	Approved
0.697	Remote Similarity	NPD4767	Approved
0.697	Remote Similarity	NPD6675	Approved
0.6966	Remote Similarity	NPD5330	Approved
0.6966	Remote Similarity	NPD7521	Approved
0.6966	Remote Similarity	NPD7146	Approved
0.6966	Remote Similarity	NPD6684	Approved
0.6966	Remote Similarity	NPD7334	Approved
0.6966	Remote Similarity	NPD6409	Approved
0.6951	Remote Similarity	NPD6926	Approved
0.6951	Remote Similarity	NPD6924	Approved
0.6947	Remote Similarity	NPD6084	Phase 2
0.6947	Remote Similarity	NPD6083	Phase 2
0.6941	Remote Similarity	NPD4195	Approved
0.6932	Remote Similarity	NPD3668	Phase 3
0.6931	Remote Similarity	NPD6012	Approved
0.6931	Remote Similarity	NPD6013	Approved
0.6931	Remote Similarity	NPD6014	Approved
0.6915	Remote Similarity	NPD5695	Phase 3
0.69	Remote Similarity	NPD5701	Approved
0.6882	Remote Similarity	NPD6399	Phase 3
0.6875	Remote Similarity	NPD6922	Approved
0.6875	Remote Similarity	NPD6923	Approved
0.6863	Remote Similarity	NPD5169	Approved
0.6863	Remote Similarity	NPD4634	Approved
0.6863	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5251	Approved
0.6863	Remote Similarity	NPD5250	Approved
0.6863	Remote Similarity	NPD5249	Phase 3
0.6863	Remote Similarity	NPD7102	Approved
0.6863	Remote Similarity	NPD6883	Approved
0.6863	Remote Similarity	NPD5248	Approved
0.6863	Remote Similarity	NPD5247	Approved
0.6863	Remote Similarity	NPD7290	Approved
0.6863	Remote Similarity	NPD5135	Approved
0.686	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4096	Approved
0.6832	Remote Similarity	NPD7320	Approved
0.6818	Remote Similarity	NPD7154	Phase 3
0.6813	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6903	Approved
0.6796	Remote Similarity	NPD5127	Approved
0.6796	Remote Similarity	NPD6847	Approved
0.6796	Remote Similarity	NPD6617	Approved
0.6796	Remote Similarity	NPD6650	Approved
0.6796	Remote Similarity	NPD6869	Approved
0.6796	Remote Similarity	NPD8130	Phase 1
0.6796	Remote Similarity	NPD5215	Approved
0.6796	Remote Similarity	NPD5217	Approved
0.6796	Remote Similarity	NPD6649	Approved
0.6796	Remote Similarity	NPD5216	Approved
0.679	Remote Similarity	NPD7144	Approved
0.679	Remote Similarity	NPD7143	Approved
0.6786	Remote Similarity	NPD6933	Approved
0.6782	Remote Similarity	NPD4139	Approved
0.6782	Remote Similarity	NPD4692	Approved
0.6778	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6411	Approved
0.6774	Remote Similarity	NPD5281	Approved
0.6774	Remote Similarity	NPD5284	Approved
0.6765	Remote Similarity	NPD6372	Approved
0.6765	Remote Similarity	NPD6373	Approved
0.6731	Remote Similarity	NPD8297	Approved
0.6731	Remote Similarity	NPD6882	Approved
0.6707	Remote Similarity	NPD7150	Approved
0.6707	Remote Similarity	NPD7152	Approved
0.6707	Remote Similarity	NPD7151	Approved
0.6701	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD1696	Phase 3
0.6667	Remote Similarity	NPD5168	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6635	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5282	Discontinued
0.6628	Remote Similarity	NPD3617	Approved
0.6604	Remote Similarity	NPD5167	Approved
0.6596	Remote Similarity	NPD7515	Phase 2
0.6585	Remote Similarity	NPD4747	Approved
0.6585	Remote Similarity	NPD4691	Approved
0.6579	Remote Similarity	NPD3198	Approved
0.6559	Remote Similarity	NPD6101	Approved
0.6559	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6929	Approved
0.6542	Remote Similarity	NPD6274	Approved
0.6538	Remote Similarity	NPD6371	Approved
0.6538	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5133	Approved
0.6512	Remote Similarity	NPD6925	Approved
0.6512	Remote Similarity	NPD6932	Approved
0.6512	Remote Similarity	NPD5776	Phase 2
0.6506	Remote Similarity	NPD5276	Approved
0.6484	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6317	Approved
0.6481	Remote Similarity	NPD6009	Approved
0.6477	Remote Similarity	NPD6931	Approved
0.6477	Remote Similarity	NPD6930	Phase 2
0.6471	Remote Similarity	NPD6008	Approved
0.6463	Remote Similarity	NPD4137	Phase 3
0.6463	Remote Similarity	NPD3698	Phase 2
0.6452	Remote Similarity	NPD5737	Approved
0.6452	Remote Similarity	NPD5208	Approved
0.6452	Remote Similarity	NPD6672	Approved
0.6437	Remote Similarity	NPD7145	Approved
0.6422	Remote Similarity	NPD6335	Approved
0.6422	Remote Similarity	NPD6314	Approved
0.6422	Remote Similarity	NPD6313	Approved
0.6413	Remote Similarity	NPD4623	Approved
0.6413	Remote Similarity	NPD4519	Discontinued
0.6413	Remote Similarity	NPD4249	Approved
0.6413	Remote Similarity	NPD6098	Approved
0.6408	Remote Similarity	NPD6412	Phase 2
0.6386	Remote Similarity	NPD4245	Approved
0.6386	Remote Similarity	NPD4244	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