NPASS Compound

Structure

CID325031 OpenBabel06191716182D 23 24 0 0 1 0 0 0 0 0999 V2000 3.4651 0.3665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 1.6471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9260 -0.7725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2054 -1.8466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5763 -2.0574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8324 -2.0574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8814 1.1783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2026 0.8754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4064 0.0015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9478 -1.4130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9043 -0.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2675 -1.2596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5120 0.0176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1619 1.0452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4604 -1.4140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4833 0.7421 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5230 1.1771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4977 -0.5528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0785 0.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6748 -1.2578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8028 1.0616 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4436 -1.0938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 15 2 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 16 14 1 6 0 0 0 17 19 1 0 0 0 0 18 12 1 1 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 4 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	4.591
LogD:	4.066
LogS:	-4.846
# Rotatable Bonds:	1
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.733
Synthetic Accessibility Score:	5.518
Fsp3:	0.6
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:	-4.692
MDCK Permeability:	2.0042125470354222e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	87.76360321044922%
Volume Distribution (VD):	1.328
Pgp-substrate:	3.045675277709961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.488
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.524
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.764
CYP3A4-substrate:	0.432

ADMET: Excretion

Clearance (CL):	4.849
Half-life (T1/2):	0.471

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.586
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.452
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.442
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.31

Download Data

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

Natural Product: NPC325031

Natural Product ID:	NPC325031
*Common Name:**	(+)-(1R,4S,10R*)-4-Hydroxycembra-2E,7E,11Z-Trien-20,10-Olide
IUPAC Name:	(1R,3E,7S,8E,10R)-7-hydroxy-3,7-dimethyl-10-propan-2-yl-15-oxabicyclo[11.2.1]hexadeca-3,8,13(16)-trien-14-one
Synonyms:
Standard InCHIKey:	KLOZYZWTTNSEEN-IBKADNNNSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-14(2)16-7-8-17-13-18(23-19(17)21)12-15(3)6-5-10-20(4,22)11-9-16/h6,9,11,13-14,16,18,22H,5,7-8,10,12H2,1-4H3/b11-9+,15-6+/t16-,18+,20-/m0/s1
SMILES:	CC1=CCCC(C=CC(CCC2=CC(C1)OC2=O)C(C)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923072
PubChem CID:	46872827
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[22032651]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22032651]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	20.8	ug.mL-1	PMID[543806]

☑ 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 NPC325031 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	182
0.1-0.2	1058
0.2-0.3	4709
0.3-0.4	11865
0.4-0.5	13029
0.5-0.6	6613
0.6-0.7	4005
0.7-0.8	1145
0.8-0.85	78
0.85-0.9	12
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC267231
0.9024	High Similarity	NPC160138
0.9	High Similarity	NPC250315
0.8947	High Similarity	NPC329852
0.8846	High Similarity	NPC93763
0.8846	High Similarity	NPC108816
0.8734	High Similarity	NPC469617
0.8718	High Similarity	NPC320630
0.8718	High Similarity	NPC7563
0.8718	High Similarity	NPC116177
0.8706	High Similarity	NPC473448
0.8659	High Similarity	NPC82297
0.8588	High Similarity	NPC212598
0.8571	High Similarity	NPC312561
0.8554	High Similarity	NPC215364
0.8554	High Similarity	NPC261380
0.8519	High Similarity	NPC42470
0.85	High Similarity	NPC178277
0.8488	Intermediate Similarity	NPC144133
0.8488	Intermediate Similarity	NPC475855
0.8488	Intermediate Similarity	NPC179394
0.8481	Intermediate Similarity	NPC57744
0.8452	Intermediate Similarity	NPC305475
0.8452	Intermediate Similarity	NPC475461
0.8452	Intermediate Similarity	NPC261721
0.8434	Intermediate Similarity	NPC476804
0.8434	Intermediate Similarity	NPC196487
0.8434	Intermediate Similarity	NPC14575
0.8421	Intermediate Similarity	NPC67183
0.8415	Intermediate Similarity	NPC85772
0.8415	Intermediate Similarity	NPC474291
0.8391	Intermediate Similarity	NPC300312
0.8391	Intermediate Similarity	NPC261607
0.8391	Intermediate Similarity	NPC111114
0.8375	Intermediate Similarity	NPC471465
0.8375	Intermediate Similarity	NPC128276
0.8375	Intermediate Similarity	NPC196653
0.8372	Intermediate Similarity	NPC106040
0.8372	Intermediate Similarity	NPC295312
0.8372	Intermediate Similarity	NPC115179
0.8354	Intermediate Similarity	NPC123360
0.8333	Intermediate Similarity	NPC476355
0.8333	Intermediate Similarity	NPC255307
0.8333	Intermediate Similarity	NPC474758
0.8315	Intermediate Similarity	NPC304886
0.8313	Intermediate Similarity	NPC473390
0.8313	Intermediate Similarity	NPC40746
0.8313	Intermediate Similarity	NPC131669
0.8313	Intermediate Similarity	NPC169575
0.8312	Intermediate Similarity	NPC163003
0.8295	Intermediate Similarity	NPC476049
0.8293	Intermediate Similarity	NPC471325
0.8289	Intermediate Similarity	NPC265574
0.8276	Intermediate Similarity	NPC281942
0.8276	Intermediate Similarity	NPC232426
0.8272	Intermediate Similarity	NPC470239
0.8272	Intermediate Similarity	NPC89128
0.8272	Intermediate Similarity	NPC470244
0.8256	Intermediate Similarity	NPC476805
0.8235	Intermediate Similarity	NPC116575
0.8235	Intermediate Similarity	NPC234038
0.8214	Intermediate Similarity	NPC191476
0.8214	Intermediate Similarity	NPC114979
0.8202	Intermediate Similarity	NPC167219
0.8193	Intermediate Similarity	NPC35556
0.8193	Intermediate Similarity	NPC229825
0.8182	Intermediate Similarity	NPC141831
0.8182	Intermediate Similarity	NPC303697
0.8182	Intermediate Similarity	NPC177037
0.8182	Intermediate Similarity	NPC472814
0.8158	Intermediate Similarity	NPC218477
0.8148	Intermediate Similarity	NPC192006
0.814	Intermediate Similarity	NPC72513
0.8132	Intermediate Similarity	NPC471462
0.8125	Intermediate Similarity	NPC271070
0.8125	Intermediate Similarity	NPC235906
0.8118	Intermediate Similarity	NPC65661
0.8118	Intermediate Similarity	NPC165162
0.8118	Intermediate Similarity	NPC86316
0.8118	Intermediate Similarity	NPC474369
0.8118	Intermediate Similarity	NPC106416
0.8118	Intermediate Similarity	NPC125290
0.8118	Intermediate Similarity	NPC470755
0.8111	Intermediate Similarity	NPC272050
0.8101	Intermediate Similarity	NPC140287
0.8101	Intermediate Similarity	NPC117746
0.8101	Intermediate Similarity	NPC259599
0.8101	Intermediate Similarity	NPC294434
0.8101	Intermediate Similarity	NPC15499
0.8095	Intermediate Similarity	NPC193198
0.8095	Intermediate Similarity	NPC53867
0.809	Intermediate Similarity	NPC228451
0.809	Intermediate Similarity	NPC125674
0.809	Intermediate Similarity	NPC115021
0.809	Intermediate Similarity	NPC475838
0.8072	Intermediate Similarity	NPC141810
0.8072	Intermediate Similarity	NPC112868
0.8072	Intermediate Similarity	NPC24417
0.8072	Intermediate Similarity	NPC52861
0.8068	Intermediate Similarity	NPC469368
0.8068	Intermediate Similarity	NPC476004
0.8068	Intermediate Similarity	NPC474761
0.8049	Intermediate Similarity	NPC617
0.8049	Intermediate Similarity	NPC167881
0.8049	Intermediate Similarity	NPC98557
0.8046	Intermediate Similarity	NPC476803
0.8025	Intermediate Similarity	NPC41780
0.8025	Intermediate Similarity	NPC65603
0.8025	Intermediate Similarity	NPC107668
0.8025	Intermediate Similarity	NPC476439
0.8025	Intermediate Similarity	NPC187568
0.8025	Intermediate Similarity	NPC470240
0.8025	Intermediate Similarity	NPC476794
0.8023	Intermediate Similarity	NPC284902
0.8023	Intermediate Similarity	NPC469483
0.8023	Intermediate Similarity	NPC122502
0.8023	Intermediate Similarity	NPC150755
0.8	Intermediate Similarity	NPC158756
0.8	Intermediate Similarity	NPC474338
0.8	Intermediate Similarity	NPC295799
0.8	Intermediate Similarity	NPC475572
0.8	Intermediate Similarity	NPC96259
0.8	Intermediate Similarity	NPC474247
0.8	Intermediate Similarity	NPC156485
0.8	Intermediate Similarity	NPC477131
0.8	Intermediate Similarity	NPC70424
0.8	Intermediate Similarity	NPC469632
0.8	Intermediate Similarity	NPC243618
0.8	Intermediate Similarity	NPC141193
0.7976	Intermediate Similarity	NPC173609
0.7976	Intermediate Similarity	NPC89555
0.7975	Intermediate Similarity	NPC269206
0.7975	Intermediate Similarity	NPC295633
0.7975	Intermediate Similarity	NPC58956
0.7955	Intermediate Similarity	NPC268298
0.7955	Intermediate Similarity	NPC5509
0.7952	Intermediate Similarity	NPC233377
0.7931	Intermediate Similarity	NPC475703
0.7931	Intermediate Similarity	NPC475678
0.7927	Intermediate Similarity	NPC299235
0.7912	Intermediate Similarity	NPC209355
0.7907	Intermediate Similarity	NPC137033
0.7907	Intermediate Similarity	NPC474547
0.7907	Intermediate Similarity	NPC21469
0.7889	Intermediate Similarity	NPC469645
0.7889	Intermediate Similarity	NPC469692
0.7889	Intermediate Similarity	NPC475912
0.7889	Intermediate Similarity	NPC139692
0.7882	Intermediate Similarity	NPC39588
0.7882	Intermediate Similarity	NPC474809
0.7882	Intermediate Similarity	NPC44261
0.7882	Intermediate Similarity	NPC59097
0.7865	Intermediate Similarity	NPC37607
0.7865	Intermediate Similarity	NPC145666
0.7865	Intermediate Similarity	NPC182136
0.7865	Intermediate Similarity	NPC51004
0.7865	Intermediate Similarity	NPC51486
0.7865	Intermediate Similarity	NPC301969
0.7865	Intermediate Similarity	NPC129419
0.7857	Intermediate Similarity	NPC59994
0.7857	Intermediate Similarity	NPC78677
0.7857	Intermediate Similarity	NPC25684
0.7857	Intermediate Similarity	NPC301477
0.7857	Intermediate Similarity	NPC281949
0.7849	Intermediate Similarity	NPC316598
0.7849	Intermediate Similarity	NPC141191
0.7848	Intermediate Similarity	NPC319163
0.7848	Intermediate Similarity	NPC129665
0.7848	Intermediate Similarity	NPC67076
0.7841	Intermediate Similarity	NPC474471
0.7841	Intermediate Similarity	NPC153805
0.7841	Intermediate Similarity	NPC475819
0.7841	Intermediate Similarity	NPC91248
0.7841	Intermediate Similarity	NPC227379
0.7841	Intermediate Similarity	NPC202672
0.7841	Intermediate Similarity	NPC260343
0.7831	Intermediate Similarity	NPC270126
0.7831	Intermediate Similarity	NPC182550
0.7831	Intermediate Similarity	NPC63649
0.7831	Intermediate Similarity	NPC264227
0.7831	Intermediate Similarity	NPC472965
0.7826	Intermediate Similarity	NPC242848
0.7826	Intermediate Similarity	NPC234993
0.7826	Intermediate Similarity	NPC230800
0.7826	Intermediate Similarity	NPC134072
0.7826	Intermediate Similarity	NPC279621
0.7821	Intermediate Similarity	NPC151481
0.7816	Intermediate Similarity	NPC107787
0.7816	Intermediate Similarity	NPC469910
0.7816	Intermediate Similarity	NPC316426
0.7816	Intermediate Similarity	NPC67493
0.7816	Intermediate Similarity	NPC315395
0.7805	Intermediate Similarity	NPC476028
0.7805	Intermediate Similarity	NPC141789
0.7805	Intermediate Similarity	NPC171204
0.7805	Intermediate Similarity	NPC97516
0.7802	Intermediate Similarity	NPC470010
0.7802	Intermediate Similarity	NPC323008
0.7802	Intermediate Similarity	NPC198853
0.7802	Intermediate Similarity	NPC81386

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 NPC325031 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1569
0.2-0.3	3668
0.3-0.4	2484
0.4-0.5	804
0.5-0.6	368
0.6-0.7	75
0.7-0.8	21
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
0.7865	Intermediate Similarity	NPD5785	Approved
0.7765	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD5363	Approved
0.7674	Intermediate Similarity	NPD5362	Discontinued
0.7674	Intermediate Similarity	NPD7154	Phase 3
0.7527	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1694	Approved
0.7356	Intermediate Similarity	NPD4270	Approved
0.7356	Intermediate Similarity	NPD4269	Approved
0.7326	Intermediate Similarity	NPD4822	Approved
0.7326	Intermediate Similarity	NPD4819	Approved
0.7326	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4820	Approved
0.7326	Intermediate Similarity	NPD4821	Approved
0.7308	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD46	Approved
0.7283	Intermediate Similarity	NPD6698	Approved
0.7241	Intermediate Similarity	NPD5369	Approved
0.7222	Intermediate Similarity	NPD5786	Approved
0.7174	Intermediate Similarity	NPD1695	Approved
0.7159	Intermediate Similarity	NPD5209	Approved
0.7129	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5779	Approved
0.7128	Intermediate Similarity	NPD5778	Approved
0.7126	Intermediate Similarity	NPD4252	Approved
0.7113	Intermediate Similarity	NPD4225	Approved
0.7111	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7838	Discovery
0.7093	Intermediate Similarity	NPD4268	Approved
0.7093	Intermediate Similarity	NPD4271	Approved
0.7087	Intermediate Similarity	NPD6371	Approved
0.7079	Intermediate Similarity	NPD5331	Approved
0.7079	Intermediate Similarity	NPD5332	Approved
0.7045	Intermediate Similarity	NPD4790	Discontinued
0.6966	Remote Similarity	NPD6435	Approved
0.6941	Remote Similarity	NPD8039	Approved
0.6939	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6686	Approved
0.6869	Remote Similarity	NPD7639	Approved
0.6869	Remote Similarity	NPD7640	Approved
0.6852	Remote Similarity	NPD7115	Discovery
0.6848	Remote Similarity	NPD4249	Approved
0.6842	Remote Similarity	NPD7983	Approved
0.6813	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6101	Approved
0.68	Remote Similarity	NPD5344	Discontinued
0.6782	Remote Similarity	NPD4756	Discovery
0.6774	Remote Similarity	NPD4250	Approved
0.6774	Remote Similarity	NPD4251	Approved
0.6768	Remote Similarity	NPD7638	Approved
0.6742	Remote Similarity	NPD5368	Approved
0.6701	Remote Similarity	NPD5282	Discontinued
0.67	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6636	Remote Similarity	NPD6053	Discontinued
0.6633	Remote Similarity	NPD5695	Phase 3
0.6598	Remote Similarity	NPD6399	Phase 3
0.6585	Remote Similarity	NPD7331	Phase 2
0.6582	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7839	Suspended
0.6542	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7748	Approved
0.6526	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6903	Approved
0.65	Remote Similarity	NPD6083	Phase 2
0.65	Remote Similarity	NPD6084	Phase 2
0.6495	Remote Similarity	NPD7637	Suspended
0.6495	Remote Similarity	NPD5693	Phase 1
0.6476	Remote Similarity	NPD5697	Approved
0.6463	Remote Similarity	NPD7341	Phase 2
0.6458	Remote Similarity	NPD5370	Suspended
0.6452	Remote Similarity	NPD3666	Approved
0.6452	Remote Similarity	NPD3665	Phase 1
0.6452	Remote Similarity	NPD3133	Approved
0.6436	Remote Similarity	NPD5696	Approved
0.6421	Remote Similarity	NPD3573	Approved
0.6415	Remote Similarity	NPD6881	Approved
0.6415	Remote Similarity	NPD6899	Approved
0.6415	Remote Similarity	NPD6011	Approved
0.6413	Remote Similarity	NPD3667	Approved
0.6374	Remote Similarity	NPD4695	Discontinued
0.6355	Remote Similarity	NPD6014	Approved
0.6355	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6013	Approved
0.6355	Remote Similarity	NPD6012	Approved
0.6354	Remote Similarity	NPD6672	Approved
0.6354	Remote Similarity	NPD5737	Approved
0.6346	Remote Similarity	NPD6647	Phase 2
0.6341	Remote Similarity	NPD3197	Phase 1
0.6337	Remote Similarity	NPD7902	Approved
0.6327	Remote Similarity	NPD6079	Approved
0.6327	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5284	Approved
0.6327	Remote Similarity	NPD5281	Approved
0.6327	Remote Similarity	NPD7515	Phase 2
0.6316	Remote Similarity	NPD5279	Phase 3
0.6316	Remote Similarity	NPD5690	Phase 2
0.6316	Remote Similarity	NPD3618	Phase 1
0.6316	Remote Similarity	NPD3172	Approved
0.631	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7290	Approved
0.6296	Remote Similarity	NPD6883	Approved
0.6296	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD368	Approved
0.6296	Remote Similarity	NPD7102	Approved
0.6277	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD5211	Phase 2
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6239	Remote Similarity	NPD6869	Approved
0.6237	Remote Similarity	NPD4223	Phase 3
0.6237	Remote Similarity	NPD4221	Approved
0.6234	Remote Similarity	NPD4266	Approved
0.6234	Remote Similarity	NPD3196	Approved
0.6234	Remote Similarity	NPD3194	Approved
0.6234	Remote Similarity	NPD3195	Phase 2
0.6226	Remote Similarity	NPD5739	Approved
0.6226	Remote Similarity	NPD6675	Approved
0.6226	Remote Similarity	NPD6402	Approved
0.6226	Remote Similarity	NPD7128	Approved
0.6224	Remote Similarity	NPD5207	Approved
0.6211	Remote Similarity	NPD1696	Phase 3
0.6186	Remote Similarity	NPD5208	Approved
0.6186	Remote Similarity	NPD4518	Approved
0.6182	Remote Similarity	NPD6882	Approved
0.6182	Remote Similarity	NPD8297	Approved
0.6168	Remote Similarity	NPD5701	Approved
0.6162	Remote Similarity	NPD5694	Approved
0.6147	Remote Similarity	NPD6420	Discontinued
0.6146	Remote Similarity	NPD6422	Discontinued
0.6139	Remote Similarity	NPD5210	Approved
0.6139	Remote Similarity	NPD4629	Approved
0.6132	Remote Similarity	NPD5141	Approved
0.6132	Remote Similarity	NPD5909	Discontinued
0.6122	Remote Similarity	NPD6051	Approved
0.6122	Remote Similarity	NPD6673	Approved
0.6122	Remote Similarity	NPD6904	Approved
0.6122	Remote Similarity	NPD6080	Approved
0.6122	Remote Similarity	NPD4753	Phase 2
0.6122	Remote Similarity	NPD5328	Approved
0.6111	Remote Similarity	NPD7320	Approved
0.6105	Remote Similarity	NPD4197	Approved
0.61	Remote Similarity	NPD4202	Approved
0.6091	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5221	Approved
0.6078	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5222	Approved
0.6064	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5692	Phase 3
0.6058	Remote Similarity	NPD5285	Approved
0.6058	Remote Similarity	NPD5286	Approved
0.6058	Remote Similarity	NPD6404	Discontinued
0.6058	Remote Similarity	NPD4696	Approved
0.6055	Remote Similarity	NPD6372	Approved
0.6055	Remote Similarity	NPD6373	Approved
0.6053	Remote Similarity	NPD6927	Phase 3
0.6042	Remote Similarity	NPD5329	Approved
0.604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7900	Approved
0.6034	Remote Similarity	NPD8516	Approved
0.6034	Remote Similarity	NPD8517	Approved
0.6034	Remote Similarity	NPD8515	Approved
0.6034	Remote Similarity	NPD8513	Phase 3
0.6024	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5173	Approved
0.6019	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3173	Approved
0.6	Remote Similarity	NPD6110	Phase 1
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2067	Discontinued
0.5982	Remote Similarity	NPD4632	Approved
0.598	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4694	Approved
0.5979	Remote Similarity	NPD5280	Approved
0.5979	Remote Similarity	NPD4688	Approved
0.5979	Remote Similarity	NPD4689	Approved
0.5979	Remote Similarity	NPD4693	Phase 3
0.5979	Remote Similarity	NPD5205	Approved
0.5979	Remote Similarity	NPD4690	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