NPASS Compound

Structure

NPC102048 OpenBabel07101719252D 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 1 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:	380.26
Volume:	407.997
LogP:	1.244
LogD:	1.806
LogS:	-3.368
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.487
Synthetic Accessibility Score:	4.799
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.16
MDCK Permeability:	2.1814492356497794e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.814
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.291
Plasma Protein Binding (PPB):	58.85421371459961%
Volume Distribution (VD):	0.879
Pgp-substrate:	38.36985778808594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.139
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.783
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.453
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	2.014
Half-life (T1/2):	0.818

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.073
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.434
Carcinogencity:	0.068
Eye Corrosion:	0.026
Eye Irritation:	0.407
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC102048

Natural Product ID:	NPC102048
*Common Name:**	19-Acetoxy-2Alpha,7Alpha, 15-Trihydroxylabda-8(17),(13Z)-Diene
IUPAC Name:	[(1S,3R,4aS,5R,7R,8aR)-3,7-dihydroxy-5-[(Z)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl acetate
Synonyms:
Standard InCHIKey:	LVWOPFFOQPENHP-QWCRRRAASA-N
Standard InCHI:	InChI=1S/C22H36O5/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/h8,17-20,23,25-26H,2,6-7,9-13H2,1,3-5H3/b14-8-/t17-,18-,19+,20-,21+,22+/m0/s1
SMILES:	C/C(=C/CO)/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:	CHEMBL452224
PubChem CID:	21672193
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	=	19.4	ug ml-1	PMID[569823]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	8.7	ug ml-1	PMID[569823]

☑ 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 NPC102048 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	175
0.1-0.2	1194
0.2-0.3	4145
0.3-0.4	10405
0.4-0.5	12073
0.5-0.6	6518
0.6-0.7	6029
0.7-0.8	2004
0.8-0.85	132
0.85-0.9	17
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC291665
0.9059	High Similarity	NPC232202
0.9	High Similarity	NPC469802
0.8941	High Similarity	NPC16265
0.8889	High Similarity	NPC170303
0.8837	High Similarity	NPC48732
0.8837	High Similarity	NPC220216
0.8765	High Similarity	NPC281880
0.875	High Similarity	NPC105490
0.8736	High Similarity	NPC124374
0.8721	High Similarity	NPC246028
0.8721	High Similarity	NPC261320
0.8718	High Similarity	NPC306727
0.869	High Similarity	NPC164424
0.8675	High Similarity	NPC476927
0.8659	High Similarity	NPC159148
0.8636	High Similarity	NPC7349
0.8636	High Similarity	NPC99653
0.8556	High Similarity	NPC276103
0.8556	High Similarity	NPC54248
0.8554	High Similarity	NPC2524
0.8554	High Similarity	NPC256112
0.8539	High Similarity	NPC474922
0.8539	High Similarity	NPC472416
0.8539	High Similarity	NPC472360
0.8523	High Similarity	NPC234335
0.8506	High Similarity	NPC170633
0.8488	Intermediate Similarity	NPC471779
0.8488	Intermediate Similarity	NPC166857
0.8478	Intermediate Similarity	NPC324841
0.8452	Intermediate Similarity	NPC79945
0.8444	Intermediate Similarity	NPC276110
0.8434	Intermediate Similarity	NPC142163
0.8427	Intermediate Similarity	NPC53555
0.8415	Intermediate Similarity	NPC242767
0.8415	Intermediate Similarity	NPC100906
0.8409	Intermediate Similarity	NPC78973
0.8387	Intermediate Similarity	NPC96784
0.8387	Intermediate Similarity	NPC235920
0.8372	Intermediate Similarity	NPC131813
0.8372	Intermediate Similarity	NPC475069
0.8372	Intermediate Similarity	NPC175145
0.8372	Intermediate Similarity	NPC329692
0.837	Intermediate Similarity	NPC325229
0.837	Intermediate Similarity	NPC275086
0.837	Intermediate Similarity	NPC247233
0.8353	Intermediate Similarity	NPC306951
0.8352	Intermediate Similarity	NPC221801
0.8352	Intermediate Similarity	NPC284194
0.8352	Intermediate Similarity	NPC211810
0.8352	Intermediate Similarity	NPC471765
0.8333	Intermediate Similarity	NPC57117
0.8315	Intermediate Similarity	NPC473675
0.8315	Intermediate Similarity	NPC477574
0.8315	Intermediate Similarity	NPC41239
0.8315	Intermediate Similarity	NPC476417
0.8313	Intermediate Similarity	NPC96362
0.8298	Intermediate Similarity	NPC109195
0.8298	Intermediate Similarity	NPC475038
0.8295	Intermediate Similarity	NPC314727
0.828	Intermediate Similarity	NPC251680
0.828	Intermediate Similarity	NPC219285
0.828	Intermediate Similarity	NPC477968
0.828	Intermediate Similarity	NPC477972
0.828	Intermediate Similarity	NPC228251
0.828	Intermediate Similarity	NPC477971
0.828	Intermediate Similarity	NPC38855
0.828	Intermediate Similarity	NPC20113
0.828	Intermediate Similarity	NPC161527
0.8272	Intermediate Similarity	NPC253190
0.8261	Intermediate Similarity	NPC473244
0.8261	Intermediate Similarity	NPC51499
0.8256	Intermediate Similarity	NPC35933
0.8242	Intermediate Similarity	NPC266899
0.8242	Intermediate Similarity	NPC37603
0.8242	Intermediate Similarity	NPC471786
0.8235	Intermediate Similarity	NPC474789
0.8235	Intermediate Similarity	NPC311070
0.8235	Intermediate Similarity	NPC52108
0.8222	Intermediate Similarity	NPC472641
0.8222	Intermediate Similarity	NPC472640
0.8214	Intermediate Similarity	NPC476646
0.8211	Intermediate Similarity	NPC473523
0.8202	Intermediate Similarity	NPC209816
0.8202	Intermediate Similarity	NPC219937
0.8202	Intermediate Similarity	NPC194485
0.8202	Intermediate Similarity	NPC53890
0.8202	Intermediate Similarity	NPC123252
0.8191	Intermediate Similarity	NPC11974
0.8191	Intermediate Similarity	NPC475617
0.8182	Intermediate Similarity	NPC104560
0.8182	Intermediate Similarity	NPC160304
0.8182	Intermediate Similarity	NPC263079
0.8172	Intermediate Similarity	NPC278673
0.8171	Intermediate Similarity	NPC283619
0.8161	Intermediate Similarity	NPC102996
0.8161	Intermediate Similarity	NPC137306
0.8161	Intermediate Similarity	NPC474970
0.8161	Intermediate Similarity	NPC473226
0.8161	Intermediate Similarity	NPC84121
0.8152	Intermediate Similarity	NPC165632
0.8152	Intermediate Similarity	NPC234993
0.8152	Intermediate Similarity	NPC134072
0.8152	Intermediate Similarity	NPC304899
0.8152	Intermediate Similarity	NPC253115
0.8148	Intermediate Similarity	NPC32832
0.814	Intermediate Similarity	NPC299963
0.8132	Intermediate Similarity	NPC119562
0.8132	Intermediate Similarity	NPC211238
0.8132	Intermediate Similarity	NPC470958
0.8132	Intermediate Similarity	NPC469491
0.8132	Intermediate Similarity	NPC470957
0.8132	Intermediate Similarity	NPC279410
0.8125	Intermediate Similarity	NPC473543
0.8118	Intermediate Similarity	NPC472504
0.8111	Intermediate Similarity	NPC472811
0.8111	Intermediate Similarity	NPC249034
0.8111	Intermediate Similarity	NPC329842
0.8111	Intermediate Similarity	NPC78594
0.8105	Intermediate Similarity	NPC475344
0.8105	Intermediate Similarity	NPC470571
0.8105	Intermediate Similarity	NPC476471
0.809	Intermediate Similarity	NPC477917
0.809	Intermediate Similarity	NPC474396
0.809	Intermediate Similarity	NPC115607
0.809	Intermediate Similarity	NPC50488
0.8085	Intermediate Similarity	NPC16601
0.8072	Intermediate Similarity	NPC239098
0.8072	Intermediate Similarity	NPC476314
0.8068	Intermediate Similarity	NPC471796
0.8068	Intermediate Similarity	NPC102640
0.8068	Intermediate Similarity	NPC245004
0.8065	Intermediate Similarity	NPC98112
0.8065	Intermediate Similarity	NPC475032
0.8065	Intermediate Similarity	NPC475033
0.8046	Intermediate Similarity	NPC476602
0.8046	Intermediate Similarity	NPC191965
0.8046	Intermediate Similarity	NPC109528
0.8043	Intermediate Similarity	NPC134067
0.8043	Intermediate Similarity	NPC474727
0.8043	Intermediate Similarity	NPC476720
0.8025	Intermediate Similarity	NPC476366
0.8025	Intermediate Similarity	NPC201048
0.8023	Intermediate Similarity	NPC23748
0.8023	Intermediate Similarity	NPC5958
0.8022	Intermediate Similarity	NPC26046
0.8022	Intermediate Similarity	NPC472812
0.8022	Intermediate Similarity	NPC38232
0.8021	Intermediate Similarity	NPC471938
0.8021	Intermediate Similarity	NPC160583
0.8021	Intermediate Similarity	NPC281378
0.8021	Intermediate Similarity	NPC95899
0.8021	Intermediate Similarity	NPC478057
0.8021	Intermediate Similarity	NPC474124
0.8	Intermediate Similarity	NPC471370
0.8	Intermediate Similarity	NPC472642
0.8	Intermediate Similarity	NPC97435
0.8	Intermediate Similarity	NPC229584
0.8	Intermediate Similarity	NPC471412
0.8	Intermediate Similarity	NPC182136
0.8	Intermediate Similarity	NPC249423
0.8	Intermediate Similarity	NPC247701
0.8	Intermediate Similarity	NPC14203
0.8	Intermediate Similarity	NPC268829
0.8	Intermediate Similarity	NPC25177
0.8	Intermediate Similarity	NPC471371
0.8	Intermediate Similarity	NPC295110
0.8	Intermediate Similarity	NPC222875
0.7979	Intermediate Similarity	NPC477928
0.7979	Intermediate Similarity	NPC477875
0.7979	Intermediate Similarity	NPC218107
0.7979	Intermediate Similarity	NPC477876
0.7978	Intermediate Similarity	NPC106332
0.7978	Intermediate Similarity	NPC472809
0.7978	Intermediate Similarity	NPC69713
0.7978	Intermediate Similarity	NPC472810
0.7976	Intermediate Similarity	NPC192999
0.7976	Intermediate Similarity	NPC476438
0.7959	Intermediate Similarity	NPC471205
0.7959	Intermediate Similarity	NPC475781
0.7957	Intermediate Similarity	NPC88009
0.7957	Intermediate Similarity	NPC202833
0.7957	Intermediate Similarity	NPC90583
0.7955	Intermediate Similarity	NPC322159
0.7955	Intermediate Similarity	NPC325594
0.7955	Intermediate Similarity	NPC202394
0.7955	Intermediate Similarity	NPC73038
0.7955	Intermediate Similarity	NPC471219
0.7952	Intermediate Similarity	NPC470758
0.7952	Intermediate Similarity	NPC132542
0.7952	Intermediate Similarity	NPC470711
0.7949	Intermediate Similarity	NPC69649
0.7949	Intermediate Similarity	NPC68703
0.7938	Intermediate Similarity	NPC471937
0.7938	Intermediate Similarity	NPC470768
0.7935	Intermediate Similarity	NPC140277
0.7935	Intermediate Similarity	NPC182826
0.7935	Intermediate Similarity	NPC105375
0.7935	Intermediate Similarity	NPC470255
0.7931	Intermediate Similarity	NPC222634

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 NPC102048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1481
0.2-0.3	3739
0.3-0.4	2447
0.4-0.5	847
0.5-0.6	247
0.6-0.7	210
0.7-0.8	26
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
0.828	Intermediate Similarity	NPD7639	Approved
0.828	Intermediate Similarity	NPD7640	Approved
0.8172	Intermediate Similarity	NPD7638	Approved
0.7727	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7637	Suspended
0.7614	Intermediate Similarity	NPD6695	Phase 3
0.7604	Intermediate Similarity	NPD4225	Approved
0.7551	Intermediate Similarity	NPD7632	Discontinued
0.7471	Intermediate Similarity	NPD7525	Registered
0.7449	Intermediate Similarity	NPD5344	Discontinued
0.7447	Intermediate Similarity	NPD5779	Approved
0.7447	Intermediate Similarity	NPD5778	Approved
0.7447	Intermediate Similarity	NPD6399	Phase 3
0.7368	Intermediate Similarity	NPD7748	Approved
0.7356	Intermediate Similarity	NPD7645	Phase 2
0.7356	Intermediate Similarity	NPD6929	Approved
0.7353	Intermediate Similarity	NPD6686	Approved
0.734	Intermediate Similarity	NPD7515	Phase 2
0.732	Intermediate Similarity	NPD7902	Approved
0.7294	Intermediate Similarity	NPD8264	Approved
0.7283	Intermediate Similarity	NPD7524	Approved
0.7283	Intermediate Similarity	NPD7750	Discontinued
0.7273	Intermediate Similarity	NPD6930	Phase 2
0.7273	Intermediate Similarity	NPD6931	Approved
0.7172	Intermediate Similarity	NPD6648	Approved
0.7128	Intermediate Similarity	NPD6051	Approved
0.7126	Intermediate Similarity	NPD6925	Approved
0.7126	Intermediate Similarity	NPD5776	Phase 2
0.7111	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7339	Approved
0.7093	Intermediate Similarity	NPD6942	Approved
0.7079	Intermediate Similarity	NPD7514	Phase 3
0.7079	Intermediate Similarity	NPD7332	Phase 2
0.7064	Intermediate Similarity	NPD7328	Approved
0.7064	Intermediate Similarity	NPD7327	Approved
0.7045	Intermediate Similarity	NPD7145	Approved
0.7011	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7900	Approved
0.701	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6902	Approved
0.7	Intermediate Similarity	NPD7516	Approved
0.699	Remote Similarity	NPD6402	Approved
0.699	Remote Similarity	NPD5739	Approved
0.699	Remote Similarity	NPD7128	Approved
0.699	Remote Similarity	NPD6675	Approved
0.6979	Remote Similarity	NPD7087	Discontinued
0.6979	Remote Similarity	NPD8035	Phase 2
0.6979	Remote Similarity	NPD8034	Phase 2
0.6979	Remote Similarity	NPD6411	Approved
0.6977	Remote Similarity	NPD6926	Approved
0.6977	Remote Similarity	NPD6924	Approved
0.6957	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4786	Approved
0.6952	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8294	Approved
0.6937	Remote Similarity	NPD8377	Approved
0.6923	Remote Similarity	NPD3667	Approved
0.6915	Remote Similarity	NPD4251	Approved
0.6915	Remote Similarity	NPD4250	Approved
0.6889	Remote Similarity	NPD7509	Discontinued
0.6889	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6893	Approved
0.6875	Remote Similarity	NPD7838	Discovery
0.6875	Remote Similarity	NPD8296	Approved
0.6875	Remote Similarity	NPD46	Approved
0.6875	Remote Similarity	NPD8335	Approved
0.6875	Remote Similarity	NPD8378	Approved
0.6875	Remote Similarity	NPD8380	Approved
0.6875	Remote Similarity	NPD8379	Approved
0.6875	Remote Similarity	NPD6698	Approved
0.6875	Remote Similarity	NPD8033	Approved
0.6857	Remote Similarity	NPD7320	Approved
0.6857	Remote Similarity	NPD6881	Approved
0.6857	Remote Similarity	NPD6899	Approved
0.6854	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6933	Approved
0.6813	Remote Similarity	NPD6898	Phase 1
0.6809	Remote Similarity	NPD7521	Approved
0.6809	Remote Similarity	NPD4249	Approved
0.6809	Remote Similarity	NPD5330	Approved
0.6809	Remote Similarity	NPD7146	Approved
0.6809	Remote Similarity	NPD3618	Phase 1
0.6809	Remote Similarity	NPD7334	Approved
0.6809	Remote Similarity	NPD6684	Approved
0.6809	Remote Similarity	NPD6409	Approved
0.6804	Remote Similarity	NPD7983	Approved
0.68	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6084	Phase 2
0.6792	Remote Similarity	NPD6373	Approved
0.6792	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6372	Approved
0.6771	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6101	Approved
0.6771	Remote Similarity	NPD5328	Approved
0.6762	Remote Similarity	NPD6412	Phase 2
0.6762	Remote Similarity	NPD5701	Approved
0.6762	Remote Similarity	NPD5697	Approved
0.6744	Remote Similarity	NPD7152	Approved
0.6744	Remote Similarity	NPD7151	Approved
0.6744	Remote Similarity	NPD7150	Approved
0.6742	Remote Similarity	NPD6932	Approved
0.6733	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7102	Approved
0.6729	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7290	Approved
0.6729	Remote Similarity	NPD6883	Approved
0.6726	Remote Similarity	NPD7503	Approved
0.6706	Remote Similarity	NPD6923	Approved
0.6706	Remote Similarity	NPD6922	Approved
0.6703	Remote Similarity	NPD4821	Approved
0.6703	Remote Similarity	NPD4819	Approved
0.6703	Remote Similarity	NPD4820	Approved
0.6703	Remote Similarity	NPD4822	Approved
0.6702	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6011	Approved
0.6697	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6638	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD6014	Approved
0.6633	Remote Similarity	NPD6079	Approved
0.6628	Remote Similarity	NPD7144	Approved
0.6628	Remote Similarity	NPD7143	Approved
0.6606	Remote Similarity	NPD6882	Approved
0.6606	Remote Similarity	NPD8297	Approved
0.6596	Remote Similarity	NPD3665	Phase 1
0.6596	Remote Similarity	NPD3133	Approved
0.6596	Remote Similarity	NPD3666	Approved
0.6593	Remote Similarity	NPD6683	Phase 2
0.6566	Remote Similarity	NPD4202	Approved
0.6545	Remote Similarity	NPD8133	Approved
0.6538	Remote Similarity	NPD5211	Phase 2
0.6518	Remote Similarity	NPD6009	Approved
0.6491	Remote Similarity	NPD6319	Approved
0.6489	Remote Similarity	NPD5332	Approved
0.6489	Remote Similarity	NPD5331	Approved
0.6484	Remote Similarity	NPD6697	Approved
0.6484	Remote Similarity	NPD6115	Approved
0.6484	Remote Similarity	NPD6114	Approved
0.6484	Remote Similarity	NPD6118	Approved
0.6471	Remote Similarity	NPD4755	Approved
0.6471	Remote Similarity	NPD7319	Approved
0.6466	Remote Similarity	NPD8328	Phase 3
0.6466	Remote Similarity	NPD7604	Phase 2
0.6463	Remote Similarity	NPD368	Approved
0.6455	Remote Similarity	NPD6053	Discontinued
0.6452	Remote Similarity	NPD4790	Discontinued
0.6449	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5695	Phase 3
0.6435	Remote Similarity	NPD5983	Phase 2
0.6422	Remote Similarity	NPD6371	Approved
0.6421	Remote Similarity	NPD3668	Phase 3
0.6415	Remote Similarity	NPD5141	Approved
0.641	Remote Similarity	NPD7492	Approved
0.6408	Remote Similarity	NPD5696	Approved
0.6392	Remote Similarity	NPD3573	Approved
0.6383	Remote Similarity	NPD6435	Approved
0.6383	Remote Similarity	NPD4269	Approved
0.6383	Remote Similarity	NPD4270	Approved
0.6374	Remote Similarity	NPD6116	Phase 1
0.6373	Remote Similarity	NPD5222	Approved
0.6373	Remote Similarity	NPD4697	Phase 3
0.6373	Remote Similarity	NPD7839	Suspended
0.6373	Remote Similarity	NPD5221	Approved
0.6373	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7136	Phase 2
0.6364	Remote Similarity	NPD3168	Discontinued
0.6364	Remote Similarity	NPD5785	Approved
0.6364	Remote Similarity	NPD4243	Approved
0.6356	Remote Similarity	NPD6616	Approved
0.6356	Remote Similarity	NPD6336	Discontinued
0.6354	Remote Similarity	NPD1694	Approved
0.6348	Remote Similarity	NPD6054	Approved
0.6348	Remote Similarity	NPD6059	Approved
0.6346	Remote Similarity	NPD5286	Approved
0.6346	Remote Similarity	NPD5285	Approved
0.6346	Remote Similarity	NPD4696	Approved
0.6346	Remote Similarity	NPD4700	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