NPASS Compound

Structure

NPC291665 OpenBabel07101718202D 27 28 0 0 1 0 0 0 0 0999 V2000 0.8660 -3.5000 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 2.3660 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 2.3660 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 0.0000 -2.0000 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 1.7321 1.0000 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 0.0000 -3.0000 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 2.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 2 0 0 0 0 3 16 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 23 2 0 0 0 0 10 19 1 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 13 27 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 24 2 0 0 0 0 16 27 1 0 0 0 0 17 25 1 6 0 0 0 18 22 1 1 0 0 0 19 26 1 6 0 0 0 20 21 1 1 0 0 0 20 22 1 0 0 0 0 21 4 1 6 0 0 0 22 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	405.361
LogP:	1.957
LogD:	1.807
LogS:	-3.916
# Rotatable Bonds:	7
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	4.878
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.115
MDCK Permeability:	1.1383588571334258e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.183
30% Bioavailability (F30%):	0.079

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	63.38568878173828%
Volume Distribution (VD):	1.144
Pgp-substrate:	33.62816619873047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.436
CYP3A4-substrate:	0.297

ADMET: Excretion

Clearance (CL):	2.694
Half-life (T1/2):	0.528

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.976
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.724
Rat Oral Acute Toxicity:	0.844
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.536
Carcinogencity:	0.395
Eye Corrosion:	0.036
Eye Irritation:	0.121
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: NPC291665

Natural Product ID:	NPC291665
*Common Name:**	19-Acetoxy-2Alpha,7Alpha-Dihydroxylabda-8(17),(13Z)-Dien-15-Al
IUPAC Name:	[(1S,3R,4aS,5R,7R,8aR)-3,7-dihydroxy-1,4a-dimethyl-6-methylidene-5-[(Z)-3-methyl-5-oxopent-3-enyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl acetate
Synonyms:
Standard InCHIKey:	XZQJBUKWKSKQAS-QWCRRRAASA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-14(8-9-23)6-7-18-15(2)19(26)10-20-21(4,13-27-16(3)24)11-17(25)12-22(18,20)5/h8-9,17-20,25-26H,2,6-7,10-13H2,1,3-5H3/b14-8-/t17-,18-,19+,20-,21+,22+/m0/s1
SMILES:	C/C(=C/C=O)/CC[C@H]1C(=C)[C@@H](C[C@H]2[C@](C)(C[C@@H](C[C@]12C)O)COC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509921
PubChem CID:	21672195
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO3153	Hyptis spicigera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917280]
NPO3153	Hyptis spicigera	Species	Lamiaceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	11.0	ug ml-1	PMID[491808]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	11.0	ug ml-1	PMID[491808]

☑ 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 NPC291665 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	188
0.1-0.2	1178
0.2-0.3	4406
0.3-0.4	10460
0.4-0.5	12023
0.5-0.6	6657
0.6-0.7	6219
0.7-0.8	1480
0.8-0.85	74
0.85-0.9	9
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC102048
0.869	High Similarity	NPC170303
0.8571	High Similarity	NPC281880
0.8571	High Similarity	NPC105490
0.8488	Intermediate Similarity	NPC476927
0.8488	Intermediate Similarity	NPC79945
0.8471	Intermediate Similarity	NPC159148
0.8462	Intermediate Similarity	NPC7349
0.8444	Intermediate Similarity	NPC232202
0.8372	Intermediate Similarity	NPC256112
0.8372	Intermediate Similarity	NPC2524
0.837	Intermediate Similarity	NPC57117
0.8353	Intermediate Similarity	NPC469802
0.8352	Intermediate Similarity	NPC473675
0.8333	Intermediate Similarity	NPC475038
0.8333	Intermediate Similarity	NPC170633
0.8333	Intermediate Similarity	NPC109195
0.8333	Intermediate Similarity	NPC16265
0.8333	Intermediate Similarity	NPC314727
0.8316	Intermediate Similarity	NPC324841
0.8315	Intermediate Similarity	NPC264546
0.8295	Intermediate Similarity	NPC164424
0.828	Intermediate Similarity	NPC276110
0.8261	Intermediate Similarity	NPC53555
0.8242	Intermediate Similarity	NPC220216
0.8242	Intermediate Similarity	NPC48732
0.8242	Intermediate Similarity	NPC78973
0.8235	Intermediate Similarity	NPC470429
0.8222	Intermediate Similarity	NPC104560
0.8214	Intermediate Similarity	NPC470428
0.8211	Intermediate Similarity	NPC325229
0.8211	Intermediate Similarity	NPC275086
0.8202	Intermediate Similarity	NPC175145
0.8202	Intermediate Similarity	NPC131813
0.8202	Intermediate Similarity	NPC475069
0.8191	Intermediate Similarity	NPC234993
0.8191	Intermediate Similarity	NPC134072
0.8182	Intermediate Similarity	NPC306951
0.8172	Intermediate Similarity	NPC119562
0.8172	Intermediate Similarity	NPC469491
0.8172	Intermediate Similarity	NPC279410
0.8152	Intermediate Similarity	NPC124374
0.8132	Intermediate Similarity	NPC261320
0.8132	Intermediate Similarity	NPC246028
0.8132	Intermediate Similarity	NPC50488
0.8132	Intermediate Similarity	NPC474396
0.8125	Intermediate Similarity	NPC251680
0.8125	Intermediate Similarity	NPC38855
0.8118	Intermediate Similarity	NPC476949
0.8105	Intermediate Similarity	NPC51499
0.809	Intermediate Similarity	NPC109528
0.8072	Intermediate Similarity	NPC306727
0.8068	Intermediate Similarity	NPC311070
0.8065	Intermediate Similarity	NPC472640
0.8065	Intermediate Similarity	NPC99653
0.8065	Intermediate Similarity	NPC472641
0.8065	Intermediate Similarity	NPC38232
0.8061	Intermediate Similarity	NPC471938
0.8061	Intermediate Similarity	NPC282233
0.8061	Intermediate Similarity	NPC95585
0.8061	Intermediate Similarity	NPC95899
0.8061	Intermediate Similarity	NPC478057
0.8046	Intermediate Similarity	NPC142163
0.8043	Intermediate Similarity	NPC182136
0.8041	Intermediate Similarity	NPC471412
0.8041	Intermediate Similarity	NPC11974
0.8023	Intermediate Similarity	NPC100906
0.8021	Intermediate Similarity	NPC218107
0.8021	Intermediate Similarity	NPC278673
0.8	Intermediate Similarity	NPC54248
0.8	Intermediate Similarity	NPC202833
0.8	Intermediate Similarity	NPC276103
0.8	Intermediate Similarity	NPC165632
0.798	Intermediate Similarity	NPC471937
0.7979	Intermediate Similarity	NPC472416
0.7979	Intermediate Similarity	NPC472360
0.7979	Intermediate Similarity	NPC474922
0.7959	Intermediate Similarity	NPC162973
0.7959	Intermediate Similarity	NPC471914
0.7957	Intermediate Similarity	NPC234335
0.7957	Intermediate Similarity	NPC472811
0.7957	Intermediate Similarity	NPC329842
0.7957	Intermediate Similarity	NPC78594
0.7957	Intermediate Similarity	NPC72845
0.7955	Intermediate Similarity	NPC224455
0.7938	Intermediate Similarity	NPC16601
0.7938	Intermediate Similarity	NPC470074
0.7938	Intermediate Similarity	NPC471413
0.7938	Intermediate Similarity	NPC471041
0.7935	Intermediate Similarity	NPC472983
0.7935	Intermediate Similarity	NPC472240
0.7935	Intermediate Similarity	NPC262858
0.7917	Intermediate Similarity	NPC99726
0.7917	Intermediate Similarity	NPC287668
0.7912	Intermediate Similarity	NPC471779
0.7912	Intermediate Similarity	NPC166857
0.7912	Intermediate Similarity	NPC471796
0.79	Intermediate Similarity	NPC218158
0.7879	Intermediate Similarity	NPC281378
0.7879	Intermediate Similarity	NPC120321
0.7879	Intermediate Similarity	NPC160583
0.7872	Intermediate Similarity	NPC476304
0.7872	Intermediate Similarity	NPC139692
0.7872	Intermediate Similarity	NPC205034
0.7872	Intermediate Similarity	NPC152778
0.7872	Intermediate Similarity	NPC162615
0.7872	Intermediate Similarity	NPC472812
0.7865	Intermediate Similarity	NPC52108
0.7865	Intermediate Similarity	NPC474789
0.7857	Intermediate Similarity	NPC247701
0.7857	Intermediate Similarity	NPC222875
0.7857	Intermediate Similarity	NPC96784
0.7857	Intermediate Similarity	NPC97435
0.7857	Intermediate Similarity	NPC25177
0.7857	Intermediate Similarity	NPC295110
0.7857	Intermediate Similarity	NPC235920
0.7857	Intermediate Similarity	NPC268829
0.7857	Intermediate Similarity	NPC303559
0.7849	Intermediate Similarity	NPC123252
0.7849	Intermediate Similarity	NPC194485
0.7849	Intermediate Similarity	NPC310479
0.7849	Intermediate Similarity	NPC472642
0.7849	Intermediate Similarity	NPC53890
0.7849	Intermediate Similarity	NPC219937
0.7843	Intermediate Similarity	NPC322912
0.7841	Intermediate Similarity	NPC90055
0.7835	Intermediate Similarity	NPC478056
0.7835	Intermediate Similarity	NPC473154
0.7835	Intermediate Similarity	NPC247233
0.7826	Intermediate Similarity	NPC106332
0.7826	Intermediate Similarity	NPC263079
0.7826	Intermediate Similarity	NPC473229
0.7826	Intermediate Similarity	NPC472810
0.7826	Intermediate Similarity	NPC160304
0.7826	Intermediate Similarity	NPC472809
0.7822	Intermediate Similarity	NPC471205
0.7816	Intermediate Similarity	NPC242767
0.7812	Intermediate Similarity	NPC471765
0.7812	Intermediate Similarity	NPC473153
0.7812	Intermediate Similarity	NPC221801
0.7812	Intermediate Similarity	NPC219353
0.7812	Intermediate Similarity	NPC304899
0.7812	Intermediate Similarity	NPC253115
0.7812	Intermediate Similarity	NPC16967
0.7812	Intermediate Similarity	NPC242848
0.7812	Intermediate Similarity	NPC471039
0.7812	Intermediate Similarity	NPC284194
0.7812	Intermediate Similarity	NPC209297
0.7812	Intermediate Similarity	NPC475380
0.7812	Intermediate Similarity	NPC211810
0.7802	Intermediate Similarity	NPC474970
0.7802	Intermediate Similarity	NPC84121
0.7802	Intermediate Similarity	NPC137306
0.7802	Intermediate Similarity	NPC329692
0.7802	Intermediate Similarity	NPC471219
0.7791	Intermediate Similarity	NPC132542
0.7791	Intermediate Similarity	NPC283619
0.7789	Intermediate Similarity	NPC140277
0.7789	Intermediate Similarity	NPC476186
0.7789	Intermediate Similarity	NPC470255
0.7789	Intermediate Similarity	NPC211238
0.7778	Intermediate Similarity	NPC32223
0.7778	Intermediate Similarity	NPC137430
0.7778	Intermediate Similarity	NPC299963
0.7778	Intermediate Similarity	NPC302360
0.7778	Intermediate Similarity	NPC476081
0.7766	Intermediate Similarity	NPC74296
0.7766	Intermediate Similarity	NPC41239
0.7766	Intermediate Similarity	NPC110923
0.7766	Intermediate Similarity	NPC476187
0.7766	Intermediate Similarity	NPC477574
0.7766	Intermediate Similarity	NPC476417
0.7755	Intermediate Similarity	NPC477968
0.7755	Intermediate Similarity	NPC477972
0.7755	Intermediate Similarity	NPC219285
0.7755	Intermediate Similarity	NPC306856
0.7755	Intermediate Similarity	NPC476767
0.7755	Intermediate Similarity	NPC161527
0.7755	Intermediate Similarity	NPC476274
0.7755	Intermediate Similarity	NPC477971
0.7755	Intermediate Similarity	NPC228251
0.7755	Intermediate Similarity	NPC477721
0.7755	Intermediate Similarity	NPC20113
0.7755	Intermediate Similarity	NPC477716
0.7755	Intermediate Similarity	NPC47024
0.7753	Intermediate Similarity	NPC472504
0.7745	Intermediate Similarity	NPC189075
0.7745	Intermediate Similarity	NPC102843
0.7745	Intermediate Similarity	NPC89171
0.7745	Intermediate Similarity	NPC275539
0.7745	Intermediate Similarity	NPC475263
0.7745	Intermediate Similarity	NPC38948
0.7745	Intermediate Similarity	NPC306265
0.7745	Intermediate Similarity	NPC88701
0.7745	Intermediate Similarity	NPC470024
0.7745	Intermediate Similarity	NPC476802
0.7742	Intermediate Similarity	NPC82876
0.7742	Intermediate Similarity	NPC146554
0.7732	Intermediate Similarity	NPC477718
0.7732	Intermediate Similarity	NPC73911

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 NPC291665 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1516
0.2-0.3	3877
0.3-0.4	2433
0.4-0.5	707
0.5-0.6	228
0.6-0.7	214
0.7-0.8	15
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
0.8125	Intermediate Similarity	NPD7639	Approved
0.8125	Intermediate Similarity	NPD7640	Approved
0.8021	Intermediate Similarity	NPD7638	Approved
0.7653	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD5344	Discontinued
0.7426	Intermediate Similarity	NPD7632	Discontinued
0.7423	Intermediate Similarity	NPD7748	Approved
0.7404	Intermediate Similarity	NPD6686	Approved
0.7396	Intermediate Similarity	NPD7515	Phase 2
0.7391	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7902	Approved
0.7283	Intermediate Similarity	NPD6695	Phase 3
0.7228	Intermediate Similarity	NPD6648	Approved
0.7216	Intermediate Similarity	NPD7637	Suspended
0.7174	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD7525	Registered
0.7075	Intermediate Similarity	NPD6881	Approved
0.7075	Intermediate Similarity	NPD6899	Approved
0.7071	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7900	Approved
0.7048	Intermediate Similarity	NPD6675	Approved
0.7048	Intermediate Similarity	NPD6402	Approved
0.7048	Intermediate Similarity	NPD7128	Approved
0.7048	Intermediate Similarity	NPD5739	Approved
0.7033	Intermediate Similarity	NPD7645	Phase 2
0.7033	Intermediate Similarity	NPD6929	Approved
0.6981	Remote Similarity	NPD5697	Approved
0.6979	Remote Similarity	NPD7750	Discontinued
0.6979	Remote Similarity	NPD7524	Approved
0.697	Remote Similarity	NPD5779	Approved
0.697	Remote Similarity	NPD5778	Approved
0.6964	Remote Similarity	NPD7327	Approved
0.6964	Remote Similarity	NPD7328	Approved
0.6957	Remote Similarity	NPD6930	Phase 2
0.6957	Remote Similarity	NPD6931	Approved
0.6944	Remote Similarity	NPD7290	Approved
0.6944	Remote Similarity	NPD7102	Approved
0.6944	Remote Similarity	NPD6883	Approved
0.6939	Remote Similarity	NPD7838	Discovery
0.6916	Remote Similarity	NPD6011	Approved
0.6916	Remote Similarity	NPD7320	Approved
0.6909	Remote Similarity	NPD4632	Approved
0.6903	Remote Similarity	NPD7516	Approved
0.6881	Remote Similarity	NPD6869	Approved
0.6881	Remote Similarity	NPD8130	Phase 1
0.6881	Remote Similarity	NPD6649	Approved
0.6881	Remote Similarity	NPD6650	Approved
0.6881	Remote Similarity	NPD6847	Approved
0.6881	Remote Similarity	NPD6617	Approved
0.6875	Remote Similarity	NPD3618	Phase 1
0.6875	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD7146	Approved
0.6875	Remote Similarity	NPD5330	Approved
0.6875	Remote Similarity	NPD6684	Approved
0.6875	Remote Similarity	NPD7521	Approved
0.6869	Remote Similarity	NPD6079	Approved
0.6863	Remote Similarity	NPD6083	Phase 2
0.6863	Remote Similarity	NPD6084	Phase 2
0.6852	Remote Similarity	NPD6372	Approved
0.6852	Remote Similarity	NPD6013	Approved
0.6852	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6373	Approved
0.6852	Remote Similarity	NPD6014	Approved
0.6852	Remote Similarity	NPD6012	Approved
0.6842	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8294	Approved
0.6842	Remote Similarity	NPD8377	Approved
0.6838	Remote Similarity	NPD7507	Approved
0.6837	Remote Similarity	NPD5328	Approved
0.6822	Remote Similarity	NPD5701	Approved
0.6822	Remote Similarity	NPD6412	Phase 2
0.6818	Remote Similarity	NPD8297	Approved
0.6818	Remote Similarity	NPD6882	Approved
0.6813	Remote Similarity	NPD6925	Approved
0.6813	Remote Similarity	NPD5776	Phase 2
0.6796	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8380	Approved
0.6783	Remote Similarity	NPD8296	Approved
0.6783	Remote Similarity	NPD8379	Approved
0.6783	Remote Similarity	NPD8378	Approved
0.6783	Remote Similarity	NPD8335	Approved
0.6783	Remote Similarity	NPD7503	Approved
0.6783	Remote Similarity	NPD8033	Approved
0.6778	Remote Similarity	NPD8264	Approved
0.6778	Remote Similarity	NPD6942	Approved
0.6778	Remote Similarity	NPD7339	Approved
0.6768	Remote Similarity	NPD46	Approved
0.6768	Remote Similarity	NPD6698	Approved
0.6765	Remote Similarity	NPD4697	Phase 3
0.6762	Remote Similarity	NPD5211	Phase 2
0.6739	Remote Similarity	NPD7145	Approved
0.6735	Remote Similarity	NPD5737	Approved
0.6735	Remote Similarity	NPD6903	Approved
0.6735	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6672	Approved
0.6729	Remote Similarity	NPD6008	Approved
0.6727	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6009	Approved
0.6726	Remote Similarity	NPD7115	Discovery
0.6703	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.67	Remote Similarity	NPD8034	Phase 2
0.67	Remote Similarity	NPD7087	Discontinued
0.67	Remote Similarity	NPD8035	Phase 2
0.67	Remote Similarity	NPD6411	Approved
0.6696	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD4786	Approved
0.6638	Remote Similarity	NPD5983	Phase 2
0.6636	Remote Similarity	NPD5141	Approved
0.6636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4202	Approved
0.6633	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3573	Approved
0.6632	Remote Similarity	NPD3667	Approved
0.661	Remote Similarity	NPD7492	Approved
0.6602	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5222	Approved
0.6602	Remote Similarity	NPD5221	Approved
0.6598	Remote Similarity	NPD6893	Approved
0.6598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7509	Discontinued
0.6596	Remote Similarity	NPD4695	Discontinued
0.6596	Remote Similarity	NPD7514	Phase 3
0.6596	Remote Similarity	NPD7332	Phase 2
0.6571	Remote Similarity	NPD5286	Approved
0.6571	Remote Similarity	NPD5285	Approved
0.6571	Remote Similarity	NPD4696	Approved
0.6555	Remote Similarity	NPD6336	Discontinued
0.6555	Remote Similarity	NPD6616	Approved
0.6552	Remote Similarity	NPD6054	Approved
0.6545	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4755	Approved
0.6538	Remote Similarity	NPD5173	Approved
0.6526	Remote Similarity	NPD6898	Phase 1
0.6526	Remote Similarity	NPD6902	Approved
0.6525	Remote Similarity	NPD8328	Phase 3
0.6522	Remote Similarity	NPD6933	Approved
0.6522	Remote Similarity	NPD6335	Approved
0.6509	Remote Similarity	NPD5223	Approved
0.6505	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD7078	Approved
0.6491	Remote Similarity	NPD6868	Approved
0.6491	Remote Similarity	NPD6274	Approved
0.6489	Remote Similarity	NPD4195	Approved
0.6486	Remote Similarity	NPD6371	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6466	Remote Similarity	NPD7100	Approved
0.6466	Remote Similarity	NPD7101	Approved
0.6465	Remote Similarity	NPD4251	Approved
0.6465	Remote Similarity	NPD4250	Approved
0.6455	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6932	Approved
0.6449	Remote Similarity	NPD5225	Approved
0.6449	Remote Similarity	NPD5224	Approved
0.6449	Remote Similarity	NPD4633	Approved
0.6449	Remote Similarity	NPD5226	Approved
0.6446	Remote Similarity	NPD7736	Approved
0.6444	Remote Similarity	NPD7152	Approved
0.6444	Remote Similarity	NPD7151	Approved
0.6444	Remote Similarity	NPD7150	Approved
0.6441	Remote Similarity	NPD6370	Approved
0.6436	Remote Similarity	NPD5785	Approved
0.6435	Remote Similarity	NPD6317	Approved
0.6429	Remote Similarity	NPD1694	Approved
0.6421	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4700	Approved
0.641	Remote Similarity	NPD6059	Approved
0.6404	Remote Similarity	NPD6923	Approved
0.6404	Remote Similarity	NPD6922	Approved
0.6389	Remote Similarity	NPD5174	Approved
0.6389	Remote Similarity	NPD5175	Approved
0.6383	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6313	Approved
0.6379	Remote Similarity	NPD6314	Approved
0.6373	Remote Similarity	NPD7983	Approved
0.6372	Remote Similarity	NPD6053	Discontinued
0.6364	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD8293	Discontinued
0.6364	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5279	Phase 3
0.6356	Remote Similarity	NPD6015	Approved
0.6356	Remote Similarity	NPD6016	Approved
0.6346	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4634	Approved
0.6337	Remote Similarity	NPD6080	Approved
0.6337	Remote Similarity	NPD6904	Approved
0.6337	Remote Similarity	NPD6673	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