NPASS Compound

Structure

NPC306265 OpenBabel07101719142D 31 33 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 7.1836 -0.8849 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 2.5981 0.5000 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 4.3301 0.5000 0.0000 C 0 0 0 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 0.0000 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 6.9757 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 0.8660 0.5000 0.0000 C 0 0 2 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 6.0622 0.5000 0.0000 C 0 0 1 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 5.1962 -1.0000 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 7.5516 2.6160 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 6.1667 1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 25 1 0 0 0 0 14 23 1 0 0 0 0 14 26 2 0 0 0 0 16 21 1 0 0 0 0 17 27 1 1 0 0 0 18 22 1 0 0 0 0 18 28 1 1 0 0 0 19 24 1 6 0 0 0 19 25 1 0 0 0 0 20 29 2 0 0 0 0 20 31 1 0 0 0 0 21 17 1 1 0 0 0 21 31 1 0 0 0 0 22 23 1 6 0 0 0 22 24 1 0 0 0 0 23 3 1 6 0 0 0 24 4 1 6 0 0 0 25 5 1 6 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.27
Volume:	457.482
LogP:	2.593
LogD:	2.981
LogS:	-3.679
# Rotatable Bonds:	6
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.394
Synthetic Accessibility Score:	5.333
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:	-5.094
MDCK Permeability:	1.6461621271446347e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.61
20% Bioavailability (F20%):	0.721
30% Bioavailability (F30%):	0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.96
Plasma Protein Binding (PPB):	75.96292877197266%
Volume Distribution (VD):	0.971
Pgp-substrate:	14.471231460571289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.582
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.612
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.429
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.788
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	7.65
Half-life (T1/2):	0.647

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.757
Carcinogencity:	0.062
Eye Corrosion:	0.006
Eye Irritation:	0.04
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC306265

Natural Product ID:	NPC306265
*Common Name:**	6Alpha,8Alpha,15(S)-Trihydroxy-23-Oxo-Labd-13(14),17-Dien-16(S),19-Olide
IUPAC Name:	(1R,4aS,5R,6R,8S,8aR)-6,8-dihydroxy-5-[(E,5S)-5-hydroxy-3-methyl-5-[(2S)-3-methyl-5-oxo-2H-furan-2-yl]pent-3-enyl]-1,4a,6-trimethyl-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carbaldehyde
Synonyms:
Standard InCHIKey:	HIPZGFJAFCRGLN-URISLNGFSA-N
Standard InCHI:	InChI=1S/C25H38O6/c1-15(11-17(27)21-16(2)12-20(29)31-21)7-8-19-24(4)10-6-9-23(3,14-26)22(24)18(28)13-25(19,5)30/h11-12,14,17-19,21-22,27-28,30H,6-10,13H2,1-5H3/b15-11+/t17-,18-,19+,21-,22-,23-,24+,25+/m0/s1
SMILES:	C/C(=C[C@@H]([C@@H]1C(=CC(=O)O1)C)O)/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:	CHEMBL497233
PubChem CID:	44157609
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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	=	3000.0	nM	PMID[525278]

☑ 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 NPC306265 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	210
0.1-0.2	1218
0.2-0.3	3663
0.3-0.4	6354
0.4-0.5	13511
0.5-0.6	7796
0.6-0.7	6788
0.7-0.8	2897
0.8-0.85	233
0.85-0.9	17
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.97	High Similarity	NPC187435
0.97	High Similarity	NPC67321
0.9596	High Similarity	NPC120321
0.9394	High Similarity	NPC303559
0.93	High Similarity	NPC476081
0.9126	High Similarity	NPC179380
0.91	High Similarity	NPC38855
0.8846	High Similarity	NPC34768
0.88	High Similarity	NPC134072
0.88	High Similarity	NPC234993
0.8704	High Similarity	NPC470063
0.87	High Similarity	NPC276110
0.8654	High Similarity	NPC159533
0.8641	High Similarity	NPC471412
0.8598	High Similarity	NPC173905
0.8598	High Similarity	NPC5475
0.8598	High Similarity	NPC284828
0.8598	High Similarity	NPC472216
0.8585	High Similarity	NPC302788
0.8585	High Similarity	NPC143609
0.8558	High Similarity	NPC295791
0.8558	High Similarity	NPC472552
0.8544	High Similarity	NPC47024
0.8544	High Similarity	NPC471413
0.8532	High Similarity	NPC269530
0.8505	High Similarity	NPC38948
0.85	High Similarity	NPC139692
0.85	High Similarity	NPC53555
0.8491	Intermediate Similarity	NPC111952
0.8485	Intermediate Similarity	NPC78973
0.8476	Intermediate Similarity	NPC23584
0.8476	Intermediate Similarity	NPC99266
0.8468	Intermediate Similarity	NPC196931
0.8468	Intermediate Similarity	NPC471816
0.8462	Intermediate Similarity	NPC472554
0.8447	Intermediate Similarity	NPC278386
0.8447	Intermediate Similarity	NPC124512
0.8447	Intermediate Similarity	NPC159763
0.844	Intermediate Similarity	NPC469655
0.844	Intermediate Similarity	NPC469656
0.844	Intermediate Similarity	NPC474846
0.8431	Intermediate Similarity	NPC242848
0.8426	Intermediate Similarity	NPC206618
0.8426	Intermediate Similarity	NPC474243
0.8426	Intermediate Similarity	NPC475065
0.8416	Intermediate Similarity	NPC57117
0.8411	Intermediate Similarity	NPC330011
0.8411	Intermediate Similarity	NPC329048
0.8396	Intermediate Similarity	NPC146731
0.8396	Intermediate Similarity	NPC296950
0.8381	Intermediate Similarity	NPC137430
0.8381	Intermediate Similarity	NPC165250
0.8381	Intermediate Similarity	NPC11956
0.8381	Intermediate Similarity	NPC472815
0.8381	Intermediate Similarity	NPC162973
0.8364	Intermediate Similarity	NPC476801
0.8364	Intermediate Similarity	NPC472002
0.835	Intermediate Similarity	NPC73911
0.8349	Intermediate Similarity	NPC5103
0.8333	Intermediate Similarity	NPC318363
0.8333	Intermediate Similarity	NPC473482
0.8333	Intermediate Similarity	NPC151393
0.8333	Intermediate Similarity	NPC472219
0.8333	Intermediate Similarity	NPC472217
0.8333	Intermediate Similarity	NPC37628
0.8333	Intermediate Similarity	NPC475418
0.8333	Intermediate Similarity	NPC472218
0.8304	Intermediate Similarity	NPC154363
0.8304	Intermediate Similarity	NPC469794
0.8304	Intermediate Similarity	NPC234858
0.8304	Intermediate Similarity	NPC72772
0.8304	Intermediate Similarity	NPC471127
0.8302	Intermediate Similarity	NPC8196
0.8302	Intermediate Similarity	NPC471208
0.8302	Intermediate Similarity	NPC156681
0.8302	Intermediate Similarity	NPC478057
0.8302	Intermediate Similarity	NPC112009
0.8302	Intermediate Similarity	NPC61442
0.8288	Intermediate Similarity	NPC469454
0.8288	Intermediate Similarity	NPC471204
0.8288	Intermediate Similarity	NPC477126
0.8288	Intermediate Similarity	NPC56448
0.8288	Intermediate Similarity	NPC469463
0.8288	Intermediate Similarity	NPC469496
0.8286	Intermediate Similarity	NPC97435
0.8286	Intermediate Similarity	NPC11974
0.8276	Intermediate Similarity	NPC67251
0.8273	Intermediate Similarity	NPC473921
0.8273	Intermediate Similarity	NPC324683
0.8273	Intermediate Similarity	NPC475668
0.8273	Intermediate Similarity	NPC475480
0.8273	Intermediate Similarity	NPC317107
0.8269	Intermediate Similarity	NPC278673
0.8269	Intermediate Similarity	NPC216478
0.8269	Intermediate Similarity	NPC222303
0.8269	Intermediate Similarity	NPC325229
0.8269	Intermediate Similarity	NPC275086
0.8261	Intermediate Similarity	NPC67569
0.8257	Intermediate Similarity	NPC273433
0.8257	Intermediate Similarity	NPC42662
0.8257	Intermediate Similarity	NPC299590
0.8252	Intermediate Similarity	NPC29952
0.8252	Intermediate Similarity	NPC202833
0.8246	Intermediate Similarity	NPC475041
0.8241	Intermediate Similarity	NPC473284
0.8241	Intermediate Similarity	NPC255387
0.8241	Intermediate Similarity	NPC475176
0.8241	Intermediate Similarity	NPC471205
0.8241	Intermediate Similarity	NPC78966
0.8241	Intermediate Similarity	NPC131665
0.8241	Intermediate Similarity	NPC301666
0.8241	Intermediate Similarity	NPC284732
0.8235	Intermediate Similarity	NPC24861
0.8235	Intermediate Similarity	NPC105490
0.823	Intermediate Similarity	NPC183580
0.823	Intermediate Similarity	NPC13713
0.823	Intermediate Similarity	NPC286528
0.823	Intermediate Similarity	NPC312824
0.823	Intermediate Similarity	NPC167606
0.823	Intermediate Similarity	NPC473968
0.823	Intermediate Similarity	NPC473590
0.823	Intermediate Similarity	NPC469684
0.823	Intermediate Similarity	NPC58662
0.823	Intermediate Similarity	NPC470492
0.823	Intermediate Similarity	NPC20302
0.823	Intermediate Similarity	NPC284068
0.823	Intermediate Similarity	NPC10721
0.823	Intermediate Similarity	NPC470493
0.823	Intermediate Similarity	NPC140055
0.8224	Intermediate Similarity	NPC258532
0.8218	Intermediate Similarity	NPC72845
0.8214	Intermediate Similarity	NPC147912
0.8214	Intermediate Similarity	NPC67259
0.8214	Intermediate Similarity	NPC472400
0.8208	Intermediate Similarity	NPC155332
0.8208	Intermediate Similarity	NPC109195
0.8208	Intermediate Similarity	NPC475038
0.8208	Intermediate Similarity	NPC32577
0.8208	Intermediate Similarity	NPC58329
0.8208	Intermediate Similarity	NPC114540
0.8205	Intermediate Similarity	NPC81736
0.8205	Intermediate Similarity	NPC172154
0.82	Intermediate Similarity	NPC174342
0.8198	Intermediate Similarity	NPC42658
0.8198	Intermediate Similarity	NPC317687
0.819	Intermediate Similarity	NPC476767
0.819	Intermediate Similarity	NPC474012
0.819	Intermediate Similarity	NPC23786
0.819	Intermediate Similarity	NPC251680
0.819	Intermediate Similarity	NPC470265
0.819	Intermediate Similarity	NPC476299
0.8182	Intermediate Similarity	NPC472215
0.8182	Intermediate Similarity	NPC478211
0.8182	Intermediate Similarity	NPC475134
0.8182	Intermediate Similarity	NPC177047
0.8182	Intermediate Similarity	NPC475563
0.8182	Intermediate Similarity	NPC472214
0.8182	Intermediate Similarity	NPC235014
0.8174	Intermediate Similarity	NPC475885
0.8173	Intermediate Similarity	NPC51499
0.8173	Intermediate Similarity	NPC175351
0.8173	Intermediate Similarity	NPC205143
0.8173	Intermediate Similarity	NPC121402
0.8173	Intermediate Similarity	NPC132753
0.8173	Intermediate Similarity	NPC224356
0.8173	Intermediate Similarity	NPC474343
0.8173	Intermediate Similarity	NPC151681
0.8173	Intermediate Similarity	NPC473963
0.8165	Intermediate Similarity	NPC181994
0.8165	Intermediate Similarity	NPC469916
0.8165	Intermediate Similarity	NPC50124
0.8165	Intermediate Similarity	NPC89171
0.8165	Intermediate Similarity	NPC275539
0.8165	Intermediate Similarity	NPC476802
0.8165	Intermediate Similarity	NPC88701
0.8165	Intermediate Similarity	NPC325054
0.8165	Intermediate Similarity	NPC472439
0.8165	Intermediate Similarity	NPC189075
0.8158	Intermediate Similarity	NPC124676
0.8158	Intermediate Similarity	NPC50774
0.8158	Intermediate Similarity	NPC146280
0.8158	Intermediate Similarity	NPC709
0.8155	Intermediate Similarity	NPC183012
0.8155	Intermediate Similarity	NPC157686
0.8155	Intermediate Similarity	NPC53565
0.8155	Intermediate Similarity	NPC259042
0.8148	Intermediate Similarity	NPC173172
0.8148	Intermediate Similarity	NPC475414
0.8148	Intermediate Similarity	NPC127609
0.8148	Intermediate Similarity	NPC477125
0.8142	Intermediate Similarity	NPC474734
0.8137	Intermediate Similarity	NPC7349
0.8137	Intermediate Similarity	NPC110022
0.8136	Intermediate Similarity	NPC293112
0.8131	Intermediate Similarity	NPC176883
0.8131	Intermediate Similarity	NPC474822
0.8131	Intermediate Similarity	NPC36688
0.8131	Intermediate Similarity	NPC476237
0.8131	Intermediate Similarity	NPC180204
0.8131	Intermediate Similarity	NPC72842

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 NPC306265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1505
0.2-0.3	3460
0.3-0.4	2468
0.4-0.5	988
0.5-0.6	281
0.6-0.7	220
0.7-0.8	44
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8447	Intermediate Similarity	NPD4225	Approved
0.8257	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.823	Intermediate Similarity	NPD7115	Discovery
0.819	Intermediate Similarity	NPD7640	Approved
0.819	Intermediate Similarity	NPD7639	Approved
0.8095	Intermediate Similarity	NPD7638	Approved
0.8018	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6686	Approved
0.7983	Intermediate Similarity	NPD7507	Approved
0.7934	Intermediate Similarity	NPD7319	Approved
0.7748	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5344	Discontinued
0.7545	Intermediate Similarity	NPD7632	Discontinued
0.7542	Intermediate Similarity	NPD7327	Approved
0.7542	Intermediate Similarity	NPD7328	Approved
0.7522	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD7516	Approved
0.7429	Intermediate Similarity	NPD46	Approved
0.7429	Intermediate Similarity	NPD6698	Approved
0.7391	Intermediate Similarity	NPD6371	Approved
0.7383	Intermediate Similarity	NPD7748	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.7355	Intermediate Similarity	NPD8033	Approved
0.7355	Intermediate Similarity	NPD8379	Approved
0.7355	Intermediate Similarity	NPD8380	Approved
0.7355	Intermediate Similarity	NPD8296	Approved
0.7355	Intermediate Similarity	NPD8378	Approved
0.7355	Intermediate Similarity	NPD8335	Approved
0.7345	Intermediate Similarity	NPD6675	Approved
0.7345	Intermediate Similarity	NPD6402	Approved
0.7345	Intermediate Similarity	NPD7128	Approved
0.7345	Intermediate Similarity	NPD5739	Approved
0.7339	Intermediate Similarity	NPD7902	Approved
0.7304	Intermediate Similarity	NPD6373	Approved
0.7304	Intermediate Similarity	NPD6372	Approved
0.729	Intermediate Similarity	NPD6399	Phase 3
0.7273	Intermediate Similarity	NPD8294	Approved
0.7273	Intermediate Similarity	NPD8377	Approved
0.7265	Intermediate Similarity	NPD8297	Approved
0.7217	Intermediate Similarity	NPD6899	Approved
0.7217	Intermediate Similarity	NPD7320	Approved
0.7217	Intermediate Similarity	NPD6881	Approved
0.7212	Intermediate Similarity	NPD3618	Phase 1
0.7207	Intermediate Similarity	NPD6648	Approved
0.7203	Intermediate Similarity	NPD4632	Approved
0.7196	Intermediate Similarity	NPD7637	Suspended
0.7182	Intermediate Similarity	NPD6083	Phase 2
0.7182	Intermediate Similarity	NPD6084	Phase 2
0.7179	Intermediate Similarity	NPD6649	Approved
0.7179	Intermediate Similarity	NPD6650	Approved
0.7143	Intermediate Similarity	NPD7524	Approved
0.7131	Intermediate Similarity	NPD6319	Approved
0.713	Intermediate Similarity	NPD5697	Approved
0.713	Intermediate Similarity	NPD5701	Approved
0.713	Intermediate Similarity	NPD5779	Approved
0.713	Intermediate Similarity	NPD5778	Approved
0.713	Intermediate Similarity	NPD6412	Phase 2
0.7115	Intermediate Similarity	NPD1694	Approved
0.7094	Intermediate Similarity	NPD6883	Approved
0.7094	Intermediate Similarity	NPD7102	Approved
0.7094	Intermediate Similarity	NPD7290	Approved
0.7091	Intermediate Similarity	NPD4697	Phase 3
0.7064	Intermediate Similarity	NPD7900	Approved
0.7064	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8133	Approved
0.7043	Intermediate Similarity	NPD6008	Approved
0.7034	Intermediate Similarity	NPD6869	Approved
0.7034	Intermediate Similarity	NPD8130	Phase 1
0.7034	Intermediate Similarity	NPD6847	Approved
0.7034	Intermediate Similarity	NPD6617	Approved
0.7009	Intermediate Similarity	NPD6012	Approved
0.7009	Intermediate Similarity	NPD6014	Approved
0.7009	Intermediate Similarity	NPD6013	Approved
0.7009	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5328	Approved
0.6983	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6053	Discontinued
0.6975	Remote Similarity	NPD6882	Approved
0.6964	Remote Similarity	NPD5696	Approved
0.696	Remote Similarity	NPD8328	Phase 3
0.6944	Remote Similarity	NPD5785	Approved
0.6935	Remote Similarity	NPD8517	Approved
0.6935	Remote Similarity	NPD8515	Approved
0.6935	Remote Similarity	NPD7503	Approved
0.6935	Remote Similarity	NPD8516	Approved
0.6935	Remote Similarity	NPD8513	Phase 3
0.693	Remote Similarity	NPD5211	Phase 2
0.6923	Remote Similarity	NPD6011	Approved
0.6923	Remote Similarity	NPD6695	Phase 3
0.6905	Remote Similarity	NPD7492	Approved
0.6891	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6684	Approved
0.6887	Remote Similarity	NPD5330	Approved
0.6887	Remote Similarity	NPD7146	Approved
0.6887	Remote Similarity	NPD6409	Approved
0.6887	Remote Similarity	NPD7334	Approved
0.6887	Remote Similarity	NPD7521	Approved
0.6885	Remote Similarity	NPD6009	Approved
0.6881	Remote Similarity	NPD6079	Approved
0.6881	Remote Similarity	NPD8035	Phase 2
0.6881	Remote Similarity	NPD8034	Phase 2
0.6875	Remote Similarity	NPD4755	Approved
0.6857	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4786	Approved
0.6855	Remote Similarity	NPD6059	Approved
0.6855	Remote Similarity	NPD6054	Approved
0.685	Remote Similarity	NPD6616	Approved
0.6847	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5695	Phase 3
0.6827	Remote Similarity	NPD3667	Approved
0.6825	Remote Similarity	NPD7604	Phase 2
0.6818	Remote Similarity	NPD4202	Approved
0.6814	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5141	Approved
0.6807	Remote Similarity	NPD4634	Approved
0.68	Remote Similarity	NPD6921	Approved
0.68	Remote Similarity	NPD5983	Phase 2
0.6797	Remote Similarity	NPD7078	Approved
0.6797	Remote Similarity	NPD8293	Discontinued
0.6792	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7838	Discovery
0.6759	Remote Similarity	NPD6672	Approved
0.6759	Remote Similarity	NPD5737	Approved
0.6759	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6903	Approved
0.6754	Remote Similarity	NPD4700	Approved
0.6754	Remote Similarity	NPD5286	Approved
0.6754	Remote Similarity	NPD4696	Approved
0.6754	Remote Similarity	NPD5285	Approved
0.6748	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6370	Approved
0.6744	Remote Similarity	NPD7736	Approved
0.6727	Remote Similarity	NPD7983	Approved
0.6727	Remote Similarity	NPD6411	Approved
0.6727	Remote Similarity	NPD5693	Phase 1
0.6719	Remote Similarity	NPD6336	Discontinued
0.6698	Remote Similarity	NPD3665	Phase 1
0.6698	Remote Similarity	NPD3133	Approved
0.6698	Remote Similarity	NPD3666	Approved
0.6697	Remote Similarity	NPD4753	Phase 2
0.6696	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.664	Remote Similarity	NPD7101	Approved
0.664	Remote Similarity	NPD7100	Approved
0.6638	Remote Similarity	NPD4633	Approved
0.6638	Remote Similarity	NPD5226	Approved
0.6638	Remote Similarity	NPD5224	Approved
0.6638	Remote Similarity	NPD5225	Approved
0.6637	Remote Similarity	NPD5221	Approved
0.6637	Remote Similarity	NPD5222	Approved
0.6637	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6930	Phase 2
0.6635	Remote Similarity	NPD6931	Approved
0.6614	Remote Similarity	NPD5988	Approved
0.6604	Remote Similarity	NPD7154	Phase 3
0.6581	Remote Similarity	NPD5174	Approved
0.6581	Remote Similarity	NPD5175	Approved
0.6579	Remote Similarity	NPD5173	Approved
0.6574	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4519	Discontinued
0.6574	Remote Similarity	NPD4623	Approved
0.656	Remote Similarity	NPD6335	Approved
0.6552	Remote Similarity	NPD5223	Approved
0.6549	Remote Similarity	NPD4629	Approved
0.6549	Remote Similarity	NPD5210	Approved
0.6545	Remote Similarity	NPD6101	Approved
0.6545	Remote Similarity	NPD6673	Approved
0.6545	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6051	Approved
0.6545	Remote Similarity	NPD6080	Approved
0.6545	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD6929	Approved
0.6535	Remote Similarity	NPD6909	Approved
0.6535	Remote Similarity	NPD6908	Approved
0.6532	Remote Similarity	NPD6868	Approved
0.6481	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5363	Approved
0.648	Remote Similarity	NPD6317	Approved
0.6476	Remote Similarity	NPD7525	Registered
0.6476	Remote Similarity	NPD7332	Phase 2
0.6476	Remote Similarity	NPD7514	Phase 3
0.6471	Remote Similarity	NPD4767	Approved
0.6471	Remote Similarity	NPD4768	Approved
0.6466	Remote Similarity	NPD7260	Phase 2
0.646	Remote Similarity	NPD6001	Approved
0.646	Remote Similarity	NPD5282	Discontinued
0.6449	Remote Similarity	NPD5362	Discontinued
0.6442	Remote Similarity	NPD6697	Approved
0.6442	Remote Similarity	NPD6114	Approved
0.6442	Remote Similarity	NPD6115	Approved
0.6442	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6118	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