NPASS Compound

Structure

NPC120321 OpenBabel07101719122D 30 32 0 0 1 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4236 -2.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6449 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 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 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6394 -0.7319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9757 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 17 2 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 23 1 0 0 0 0 15 26 2 0 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 18 27 1 6 0 0 0 19 9 1 1 0 0 0 19 30 1 0 0 0 0 20 24 1 1 0 0 0 20 25 1 0 0 0 0 21 28 2 0 0 0 0 21 30 1 0 0 0 0 22 23 1 1 0 0 0 22 24 1 0 0 0 0 23 3 1 1 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.27
Volume:	448.692
LogP:	3.492
LogD:	3.76
LogS:	-4.077
# Rotatable Bonds:	6
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	5.094
Fsp3:	0.72
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.004
MDCK Permeability:	2.380334262852557e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.131
20% Bioavailability (F20%):	0.584
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.822
Plasma Protein Binding (PPB):	80.53985595703125%
Volume Distribution (VD):	0.825
Pgp-substrate:	11.874235153198242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.295
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.588
CYP2C9-inhibitor:	0.093
CYP2C9-substrate:	0.638
CYP2D6-inhibitor:	0.367
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	7.508
Half-life (T1/2):	0.568

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.169
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.538
Skin Sensitization:	0.932
Carcinogencity:	0.04
Eye Corrosion:	0.026
Eye Irritation:	0.087
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC120321

Natural Product ID:	NPC120321
*Common Name:**	6Alpha,8Alpha-Dihydroxy-23-Oxo-Labd-13(14),17-Dien-16(R),19-Olide
IUPAC Name:	(1R,4aS,5R,6R,8S,8aR)-6,8-dihydroxy-1,4a,6-trimethyl-5-[(E)-3-methyl-5-[(2R)-3-methyl-5-oxo-2H-furan-2-yl]pent-3-enyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carbaldehyde
Synonyms:
Standard InCHIKey:	BILUXNZIXILZTL-FTZSKZMTSA-N
Standard InCHI:	InChI=1S/C25H38O5/c1-16(7-9-19-17(2)13-21(28)30-19)8-10-20-24(4)12-6-11-23(3,15-26)22(24)18(27)14-25(20,5)29/h7,13,15,18-20,22,27,29H,6,8-12,14H2,1-5H3/b16-7+/t18-,19+,20+,22-,23-,24+,25+/m0/s1
SMILES:	C/C(=CC[C@@H]1C(=CC(=O)O1)C)/CC[C@@H]1[C@@]2(C)CCC[C@@](C)(C=O)[C@@H]2[C@H](C[C@@]1(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497036
PubChem CID:	44157594
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
NPO33075	salvia dominica	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19459643]

☑ 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
Kd	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6478	Individual Protein	Tubulin--tyrosine ligase	Homo sapiens	Kd	=	810.0	nM	PMID[457261]

☑ 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 NPC120321 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	204
0.1-0.2	1194
0.2-0.3	3785
0.3-0.4	6617
0.4-0.5	14179
0.5-0.6	6998
0.6-0.7	6553
0.7-0.8	2898
0.8-0.85	227
0.85-0.9	27
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC476081
0.9596	High Similarity	NPC306265
0.9495	High Similarity	NPC179380
0.93	High Similarity	NPC187435
0.93	High Similarity	NPC67321
0.92	High Similarity	NPC34768
0.9062	High Similarity	NPC276110
0.899	High Similarity	NPC471412
0.899	High Similarity	NPC303559
0.8969	High Similarity	NPC234993
0.8969	High Similarity	NPC134072
0.8922	High Similarity	NPC302788
0.8889	High Similarity	NPC471413
0.8889	High Similarity	NPC47024
0.8854	High Similarity	NPC139692
0.8713	High Similarity	NPC165250
0.8713	High Similarity	NPC162973
0.87	High Similarity	NPC38855
0.8646	High Similarity	NPC78973
0.8627	High Similarity	NPC112009
0.8611	High Similarity	NPC72772
0.8611	High Similarity	NPC469794
0.86	High Similarity	NPC216478
0.86	High Similarity	NPC278673
0.8586	High Similarity	NPC29952
0.8586	High Similarity	NPC242848
0.8571	High Similarity	NPC57117
0.8571	High Similarity	NPC105490
0.8571	High Similarity	NPC474243
0.8557	High Similarity	NPC72845
0.8542	High Similarity	NPC174342
0.8529	High Similarity	NPC114540
0.8529	High Similarity	NPC155332
0.8529	High Similarity	NPC32577
0.8515	High Similarity	NPC476299
0.8515	High Similarity	NPC474012
0.8505	High Similarity	NPC470063
0.85	High Similarity	NPC132753
0.85	High Similarity	NPC175351
0.85	High Similarity	NPC473963
0.85	High Similarity	NPC151681
0.85	High Similarity	NPC121402
0.85	High Similarity	NPC224356
0.85	High Similarity	NPC51499
0.8485	Intermediate Similarity	NPC157686
0.8485	Intermediate Similarity	NPC259042
0.8485	Intermediate Similarity	NPC183012
0.8476	Intermediate Similarity	NPC476802
0.8476	Intermediate Similarity	NPC89171
0.8476	Intermediate Similarity	NPC189075
0.8476	Intermediate Similarity	NPC275539
0.8469	Intermediate Similarity	NPC7349
0.8447	Intermediate Similarity	NPC176883
0.8447	Intermediate Similarity	NPC471208
0.8447	Intermediate Similarity	NPC180204
0.8447	Intermediate Similarity	NPC36688
0.8447	Intermediate Similarity	NPC45897
0.8447	Intermediate Similarity	NPC478057
0.844	Intermediate Similarity	NPC196931
0.8421	Intermediate Similarity	NPC131813
0.8416	Intermediate Similarity	NPC476807
0.8416	Intermediate Similarity	NPC275086
0.8416	Intermediate Similarity	NPC476806
0.8416	Intermediate Similarity	NPC325229
0.8411	Intermediate Similarity	NPC474846
0.8411	Intermediate Similarity	NPC469655
0.8411	Intermediate Similarity	NPC469656
0.84	Intermediate Similarity	NPC472363
0.84	Intermediate Similarity	NPC472362
0.84	Intermediate Similarity	NPC202833
0.84	Intermediate Similarity	NPC93245
0.84	Intermediate Similarity	NPC473964
0.84	Intermediate Similarity	NPC154526
0.8396	Intermediate Similarity	NPC5475
0.8396	Intermediate Similarity	NPC173905
0.8396	Intermediate Similarity	NPC284828
0.8396	Intermediate Similarity	NPC472216
0.8384	Intermediate Similarity	NPC225474
0.8384	Intermediate Similarity	NPC469596
0.8384	Intermediate Similarity	NPC148000
0.8384	Intermediate Similarity	NPC24861
0.8381	Intermediate Similarity	NPC143609
0.8381	Intermediate Similarity	NPC110496
0.835	Intermediate Similarity	NPC472552
0.835	Intermediate Similarity	NPC273005
0.835	Intermediate Similarity	NPC109195
0.835	Intermediate Similarity	NPC58329
0.835	Intermediate Similarity	NPC31058
0.835	Intermediate Similarity	NPC475038
0.835	Intermediate Similarity	NPC469606
0.8333	Intermediate Similarity	NPC251680
0.8333	Intermediate Similarity	NPC117685
0.8333	Intermediate Similarity	NPC201406
0.8333	Intermediate Similarity	NPC476767
0.8317	Intermediate Similarity	NPC474343
0.8317	Intermediate Similarity	NPC136781
0.8317	Intermediate Similarity	NPC73911
0.8302	Intermediate Similarity	NPC325054
0.8302	Intermediate Similarity	NPC476479
0.8286	Intermediate Similarity	NPC469607
0.8286	Intermediate Similarity	NPC111952
0.8283	Intermediate Similarity	NPC205034
0.8283	Intermediate Similarity	NPC152778
0.8283	Intermediate Similarity	NPC162615
0.8273	Intermediate Similarity	NPC471816
0.8269	Intermediate Similarity	NPC189588
0.8269	Intermediate Similarity	NPC97487
0.8269	Intermediate Similarity	NPC10232
0.8269	Intermediate Similarity	NPC120009
0.8269	Intermediate Similarity	NPC476237
0.8269	Intermediate Similarity	NPC196471
0.8269	Intermediate Similarity	NPC159533
0.8269	Intermediate Similarity	NPC23584
0.8269	Intermediate Similarity	NPC222153
0.8269	Intermediate Similarity	NPC187302
0.8265	Intermediate Similarity	NPC232202
0.8257	Intermediate Similarity	NPC25909
0.8252	Intermediate Similarity	NPC472554
0.8252	Intermediate Similarity	NPC11974
0.8252	Intermediate Similarity	NPC235142
0.8252	Intermediate Similarity	NPC115899
0.8247	Intermediate Similarity	NPC104560
0.8247	Intermediate Similarity	NPC473229
0.8235	Intermediate Similarity	NPC478056
0.8235	Intermediate Similarity	NPC108368
0.8235	Intermediate Similarity	NPC57079
0.8235	Intermediate Similarity	NPC316598
0.8235	Intermediate Similarity	NPC119036
0.8235	Intermediate Similarity	NPC218107
0.8224	Intermediate Similarity	NPC475065
0.8218	Intermediate Similarity	NPC284518
0.8218	Intermediate Similarity	NPC165632
0.8218	Intermediate Similarity	NPC16967
0.8208	Intermediate Similarity	NPC329048
0.8208	Intermediate Similarity	NPC330011
0.82	Intermediate Similarity	NPC250075
0.8182	Intermediate Similarity	NPC238667
0.8182	Intermediate Similarity	NPC177037
0.8182	Intermediate Similarity	NPC233345
0.8182	Intermediate Similarity	NPC473944
0.8182	Intermediate Similarity	NPC186363
0.8182	Intermediate Similarity	NPC472814
0.8173	Intermediate Similarity	NPC11956
0.8173	Intermediate Similarity	NPC477054
0.8173	Intermediate Similarity	NPC476769
0.8173	Intermediate Similarity	NPC137430
0.8173	Intermediate Similarity	NPC295791
0.8165	Intermediate Similarity	NPC12046
0.8165	Intermediate Similarity	NPC476801
0.8165	Intermediate Similarity	NPC4573
0.8165	Intermediate Similarity	NPC269530
0.8165	Intermediate Similarity	NPC277769
0.8165	Intermediate Similarity	NPC194951
0.8165	Intermediate Similarity	NPC69291
0.8163	Intermediate Similarity	NPC116620
0.8163	Intermediate Similarity	NPC50488
0.8163	Intermediate Similarity	NPC474396
0.8163	Intermediate Similarity	NPC194642
0.8163	Intermediate Similarity	NPC5509
0.8163	Intermediate Similarity	NPC314727
0.8155	Intermediate Similarity	NPC470906
0.8155	Intermediate Similarity	NPC470761
0.8155	Intermediate Similarity	NPC16601
0.8155	Intermediate Similarity	NPC476303
0.8155	Intermediate Similarity	NPC324841
0.8155	Intermediate Similarity	NPC473219
0.8155	Intermediate Similarity	NPC266955
0.8155	Intermediate Similarity	NPC54705
0.8155	Intermediate Similarity	NPC470074
0.8148	Intermediate Similarity	NPC478209
0.8148	Intermediate Similarity	NPC179642
0.8148	Intermediate Similarity	NPC472666
0.8148	Intermediate Similarity	NPC472214
0.8148	Intermediate Similarity	NPC472215
0.8144	Intermediate Similarity	NPC166857
0.8144	Intermediate Similarity	NPC312561
0.8137	Intermediate Similarity	NPC253826
0.8137	Intermediate Similarity	NPC291634
0.8137	Intermediate Similarity	NPC91695
0.8137	Intermediate Similarity	NPC110937
0.8137	Intermediate Similarity	NPC100912
0.8137	Intermediate Similarity	NPC70145
0.8137	Intermediate Similarity	NPC126815
0.8131	Intermediate Similarity	NPC472219
0.8131	Intermediate Similarity	NPC38948
0.8131	Intermediate Similarity	NPC472217
0.8131	Intermediate Similarity	NPC322903
0.8131	Intermediate Similarity	NPC475418
0.8131	Intermediate Similarity	NPC90946
0.8131	Intermediate Similarity	NPC318363
0.8131	Intermediate Similarity	NPC472218
0.8131	Intermediate Similarity	NPC473482
0.8131	Intermediate Similarity	NPC300614
0.8125	Intermediate Similarity	NPC65661
0.8125	Intermediate Similarity	NPC86316
0.8125	Intermediate Similarity	NPC106416
0.8119	Intermediate Similarity	NPC266899
0.8119	Intermediate Similarity	NPC279974
0.8113	Intermediate Similarity	NPC119855
0.8113	Intermediate Similarity	NPC266570

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 NPC120321 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1482
0.2-0.3	3474
0.3-0.4	2495
0.4-0.5	984
0.5-0.6	261
0.6-0.7	210
0.7-0.8	63
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8416	Intermediate Similarity	NPD7638	Approved
0.8333	Intermediate Similarity	NPD7640	Approved
0.8333	Intermediate Similarity	NPD7639	Approved
0.8058	Intermediate Similarity	NPD4225	Approved
0.8056	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD7115	Discovery
0.7812	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6686	Approved
0.7797	Intermediate Similarity	NPD7507	Approved
0.775	Intermediate Similarity	NPD7319	Approved
0.7706	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7748	Approved
0.7664	Intermediate Similarity	NPD7632	Discontinued
0.7647	Intermediate Similarity	NPD7515	Phase 2
0.7619	Intermediate Similarity	NPD7902	Approved
0.7615	Intermediate Similarity	NPD6675	Approved
0.7615	Intermediate Similarity	NPD7128	Approved
0.7615	Intermediate Similarity	NPD6402	Approved
0.7615	Intermediate Similarity	NPD5739	Approved
0.7573	Intermediate Similarity	NPD6399	Phase 3
0.7568	Intermediate Similarity	NPD6372	Approved
0.7568	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD3618	Phase 1
0.7477	Intermediate Similarity	NPD6881	Approved
0.7477	Intermediate Similarity	NPD6899	Approved
0.7477	Intermediate Similarity	NPD7320	Approved
0.7453	Intermediate Similarity	NPD6083	Phase 2
0.7453	Intermediate Similarity	NPD6084	Phase 2
0.7434	Intermediate Similarity	NPD6650	Approved
0.7434	Intermediate Similarity	NPD6649	Approved
0.74	Intermediate Similarity	NPD1694	Approved
0.7387	Intermediate Similarity	NPD5701	Approved
0.7387	Intermediate Similarity	NPD5697	Approved
0.7358	Intermediate Similarity	NPD4697	Phase 3
0.735	Intermediate Similarity	NPD7328	Approved
0.735	Intermediate Similarity	NPD7327	Approved
0.7345	Intermediate Similarity	NPD7290	Approved
0.7345	Intermediate Similarity	NPD6883	Approved
0.7345	Intermediate Similarity	NPD7102	Approved
0.7333	Intermediate Similarity	NPD7900	Approved
0.7333	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7637	Suspended
0.7297	Intermediate Similarity	NPD6008	Approved
0.7288	Intermediate Similarity	NPD7516	Approved
0.7282	Intermediate Similarity	NPD5328	Approved
0.7281	Intermediate Similarity	NPD6869	Approved
0.7281	Intermediate Similarity	NPD6617	Approved
0.7281	Intermediate Similarity	NPD6847	Approved
0.7281	Intermediate Similarity	NPD8130	Phase 1
0.7257	Intermediate Similarity	NPD6012	Approved
0.7257	Intermediate Similarity	NPD6013	Approved
0.7257	Intermediate Similarity	NPD6014	Approved
0.7248	Intermediate Similarity	NPD5344	Discontinued
0.7238	Intermediate Similarity	NPD5778	Approved
0.7238	Intermediate Similarity	NPD5779	Approved
0.7222	Intermediate Similarity	NPD5696	Approved
0.7217	Intermediate Similarity	NPD6053	Discontinued
0.7217	Intermediate Similarity	NPD6882	Approved
0.7217	Intermediate Similarity	NPD8297	Approved
0.7212	Intermediate Similarity	NPD6698	Approved
0.7212	Intermediate Similarity	NPD46	Approved
0.7168	Intermediate Similarity	NPD6011	Approved
0.7167	Intermediate Similarity	NPD8296	Approved
0.7167	Intermediate Similarity	NPD8033	Approved
0.7167	Intermediate Similarity	NPD8335	Approved
0.7167	Intermediate Similarity	NPD8380	Approved
0.7167	Intermediate Similarity	NPD8379	Approved
0.7167	Intermediate Similarity	NPD8378	Approved
0.7157	Intermediate Similarity	NPD7521	Approved
0.7157	Intermediate Similarity	NPD7146	Approved
0.7157	Intermediate Similarity	NPD6409	Approved
0.7157	Intermediate Similarity	NPD7334	Approved
0.7157	Intermediate Similarity	NPD6684	Approved
0.7157	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.713	Intermediate Similarity	NPD4755	Approved
0.713	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4786	Approved
0.7103	Intermediate Similarity	NPD5695	Phase 3
0.7103	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3667	Approved
0.7083	Intermediate Similarity	NPD8294	Approved
0.7083	Intermediate Similarity	NPD8377	Approved
0.7075	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5785	Approved
0.7043	Intermediate Similarity	NPD6371	Approved
0.703	Intermediate Similarity	NPD6695	Phase 3
0.7027	Intermediate Similarity	NPD5211	Phase 2
0.7019	Intermediate Similarity	NPD5737	Approved
0.7019	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6903	Approved
0.7019	Intermediate Similarity	NPD6672	Approved
0.7009	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD6648	Approved
0.7	Intermediate Similarity	NPD5286	Approved
0.7	Intermediate Similarity	NPD4700	Approved
0.7	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD5285	Approved
0.6981	Remote Similarity	NPD6411	Approved
0.6981	Remote Similarity	NPD5693	Phase 1
0.6961	Remote Similarity	NPD3665	Phase 1
0.6961	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3666	Approved
0.6961	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3133	Approved
0.6952	Remote Similarity	NPD4753	Phase 2
0.6944	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6319	Approved
0.693	Remote Similarity	NPD6412	Phase 2
0.6923	Remote Similarity	NPD3573	Approved
0.6903	Remote Similarity	NPD5141	Approved
0.6891	Remote Similarity	NPD6274	Approved
0.6881	Remote Similarity	NPD5222	Approved
0.6881	Remote Similarity	NPD5221	Approved
0.6881	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5225	Approved
0.6875	Remote Similarity	NPD5226	Approved
0.6875	Remote Similarity	NPD5224	Approved
0.6875	Remote Similarity	NPD4633	Approved
0.6864	Remote Similarity	NPD8133	Approved
0.686	Remote Similarity	NPD7101	Approved
0.686	Remote Similarity	NPD7100	Approved
0.6855	Remote Similarity	NPD7492	Approved
0.6833	Remote Similarity	NPD6009	Approved
0.6827	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5173	Approved
0.6814	Remote Similarity	NPD5175	Approved
0.6814	Remote Similarity	NPD5174	Approved
0.681	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6059	Approved
0.6803	Remote Similarity	NPD6054	Approved
0.68	Remote Similarity	NPD6616	Approved
0.6792	Remote Similarity	NPD6080	Approved
0.6792	Remote Similarity	NPD6051	Approved
0.6792	Remote Similarity	NPD6673	Approved
0.6792	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6904	Approved
0.6792	Remote Similarity	NPD6101	Approved
0.6789	Remote Similarity	NPD4629	Approved
0.6789	Remote Similarity	NPD5210	Approved
0.6786	Remote Similarity	NPD5223	Approved
0.6783	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6335	Approved
0.6774	Remote Similarity	NPD8328	Phase 3
0.6774	Remote Similarity	NPD7604	Phase 2
0.6762	Remote Similarity	NPD7750	Discontinued
0.6762	Remote Similarity	NPD7524	Approved
0.6752	Remote Similarity	NPD4634	Approved
0.675	Remote Similarity	NPD6868	Approved
0.6748	Remote Similarity	NPD5983	Phase 2
0.6748	Remote Similarity	NPD7503	Approved
0.6748	Remote Similarity	NPD6908	Approved
0.6748	Remote Similarity	NPD6909	Approved
0.6746	Remote Similarity	NPD8293	Discontinued
0.6746	Remote Similarity	NPD7078	Approved
0.6733	Remote Similarity	NPD6930	Phase 2
0.6733	Remote Similarity	NPD7525	Registered
0.6733	Remote Similarity	NPD6931	Approved
0.67	Remote Similarity	NPD6114	Approved
0.67	Remote Similarity	NPD6115	Approved
0.67	Remote Similarity	NPD6118	Approved
0.67	Remote Similarity	NPD6697	Approved
0.6699	Remote Similarity	NPD7154	Phase 3
0.6697	Remote Similarity	NPD5282	Discontinued
0.6697	Remote Similarity	NPD6001	Approved
0.6696	Remote Similarity	NPD4767	Approved
0.6696	Remote Similarity	NPD4768	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6694	Remote Similarity	NPD6317	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD5284	Approved
0.6639	Remote Similarity	NPD6314	Approved
0.6639	Remote Similarity	NPD6313	Approved
0.6636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3668	Phase 3
0.6634	Remote Similarity	NPD6929	Approved
0.6634	Remote Similarity	NPD7645	Phase 2
0.6613	Remote Similarity	NPD6015	Approved
0.6613	Remote Similarity	NPD6016	Approved
0.6613	Remote Similarity	NPD6921	Approved
0.6613	Remote Similarity	NPD8517	Approved
0.6613	Remote Similarity	NPD8515	Approved
0.6613	Remote Similarity	NPD8516	Approved
0.6613	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8513	Phase 3
0.6607	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4223	Phase 3
0.6602	Remote Similarity	NPD4221	Approved
0.6581	Remote Similarity	NPD4729	Approved
0.6581	Remote Similarity	NPD4730	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