NPASS Compound

Structure

NPC79945 OpenBabel07101719402D 21 22 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 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 -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 -2.5981 -3.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 4 6 1 0 0 0 0 4 11 1 0 0 0 0 5 7 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 12 16 1 6 0 0 0 13 16 1 6 0 0 0 13 17 1 0 0 0 0 14 17 1 6 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 2 1 6 0 0 0 17 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.18
Volume:	312.727
LogP:	1.853
LogD:	0.697
LogS:	-3.109
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.699
Synthetic Accessibility Score:	4.064
Fsp3:	0.706
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:	-5.238
MDCK Permeability:	1.640307527850382e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.602
Human Intestinal Absorption (HIA):	0.5
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.845
Plasma Protein Binding (PPB):	85.38684844970703%
Volume Distribution (VD):	0.352
Pgp-substrate:	16.00316047668457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.225
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.331
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.24
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.289
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	3.861
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.563
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.938
Carcinogencity:	0.084
Eye Corrosion:	0.094
Eye Irritation:	0.676
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC79945

Natural Product ID:	NPC79945
*Common Name:**	3-((1R,4As,5R,6R,8Ar)-6-Hydroxy-5-(Hydroxymethyl)-5,8A-Dimethyl-2-Methylene-Decahydronaphthalen-1-Yl)Acrylic Acid
IUPAC Name:	(E)-3-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]prop-2-enoic acid
Synonyms:
Standard InCHIKey:	ABRILZQPRHWMRY-JOAVWQPASA-N
Standard InCHI:	InChI=1S/C17H26O4/c1-11-4-6-13-16(2,12(11)5-7-15(20)21)9-8-14(19)17(13,3)10-18/h5,7,12-14,18-19H,1,4,6,8-10H2,2-3H3,(H,20,21)/b7-5+/t12-,13+,14-,16+,17+/m1/s1
SMILES:	OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2/C=C/C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503611
PubChem CID:	44577210
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

*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
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	root	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	aerial parts	purchased in Juhuacun herbal market, Kunming, Yunnan Province, China	2002-Oct	PMID[16562826]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18357994]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21598983]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22026410]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377022]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3578	Andrographis paniculata	Species	Acanthaceae	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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	28810.0	nM	PMID[567453]

☑ 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 NPC79945 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	169
0.1-0.2	1059
0.2-0.3	4239
0.3-0.4	11013
0.4-0.5	12258
0.5-0.6	6881
0.6-0.7	5037
0.7-0.8	1831
0.8-0.85	153
0.85-0.9	47
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC281880
0.9241	High Similarity	NPC159148
0.9157	High Similarity	NPC104560
0.9125	High Similarity	NPC2524
0.9024	High Similarity	NPC109528
0.9	High Similarity	NPC170303
0.8916	High Similarity	NPC475069
0.8916	High Similarity	NPC175145
0.8916	High Similarity	NPC131813
0.8902	High Similarity	NPC302360
0.8824	High Similarity	NPC314727
0.878	High Similarity	NPC57370
0.878	High Similarity	NPC476927
0.8736	High Similarity	NPC152778
0.8736	High Similarity	NPC162615
0.8736	High Similarity	NPC205034
0.8721	High Similarity	NPC78973
0.8659	High Similarity	NPC256112
0.8636	High Similarity	NPC191521
0.8625	High Similarity	NPC476949
0.8621	High Similarity	NPC72845
0.8605	High Similarity	NPC262858
0.8605	High Similarity	NPC472240
0.8554	High Similarity	NPC311070
0.8523	High Similarity	NPC139692
0.8523	High Similarity	NPC472812
0.8523	High Similarity	NPC476304
0.8506	High Similarity	NPC182136
0.8506	High Similarity	NPC310479
0.85	High Similarity	NPC470428
0.85	High Similarity	NPC132542
0.8488	Intermediate Similarity	NPC229612
0.8488	Intermediate Similarity	NPC7280
0.8488	Intermediate Similarity	NPC291665
0.8452	Intermediate Similarity	NPC102048
0.8452	Intermediate Similarity	NPC306951
0.8444	Intermediate Similarity	NPC242848
0.8444	Intermediate Similarity	NPC234993
0.8444	Intermediate Similarity	NPC195366
0.8444	Intermediate Similarity	NPC301534
0.8444	Intermediate Similarity	NPC250757
0.8444	Intermediate Similarity	NPC114743
0.8444	Intermediate Similarity	NPC16967
0.8444	Intermediate Similarity	NPC473153
0.8444	Intermediate Similarity	NPC134072
0.8434	Intermediate Similarity	NPC224455
0.8427	Intermediate Similarity	NPC119562
0.8427	Intermediate Similarity	NPC476186
0.8427	Intermediate Similarity	NPC57117
0.8427	Intermediate Similarity	NPC279410
0.8409	Intermediate Similarity	NPC74296
0.8409	Intermediate Similarity	NPC110923
0.8409	Intermediate Similarity	NPC472811
0.8391	Intermediate Similarity	NPC50488
0.8391	Intermediate Similarity	NPC146554
0.8391	Intermediate Similarity	NPC474396
0.8391	Intermediate Similarity	NPC82876
0.8372	Intermediate Similarity	NPC166857
0.8353	Intermediate Similarity	NPC476602
0.8352	Intermediate Similarity	NPC99726
0.8315	Intermediate Similarity	NPC214697
0.8315	Intermediate Similarity	NPC38232
0.8315	Intermediate Similarity	NPC53555
0.8313	Intermediate Similarity	NPC142163
0.8293	Intermediate Similarity	NPC470429
0.828	Intermediate Similarity	NPC282524
0.8276	Intermediate Similarity	NPC472810
0.8276	Intermediate Similarity	NPC472809
0.8272	Intermediate Similarity	NPC85105
0.8272	Intermediate Similarity	NPC149550
0.8261	Intermediate Similarity	NPC278386
0.8261	Intermediate Similarity	NPC124512
0.8261	Intermediate Similarity	NPC474440
0.8261	Intermediate Similarity	NPC159763
0.8256	Intermediate Similarity	NPC473226
0.8256	Intermediate Similarity	NPC82979
0.8222	Intermediate Similarity	NPC470255
0.8202	Intermediate Similarity	NPC329842
0.8202	Intermediate Similarity	NPC212948
0.8202	Intermediate Similarity	NPC472978
0.8182	Intermediate Similarity	NPC16265
0.8171	Intermediate Similarity	NPC198240
0.8152	Intermediate Similarity	NPC73911
0.8152	Intermediate Similarity	NPC253826
0.8148	Intermediate Similarity	NPC253190
0.8132	Intermediate Similarity	NPC472441
0.8132	Intermediate Similarity	NPC180950
0.8132	Intermediate Similarity	NPC276110
0.8125	Intermediate Similarity	NPC201048
0.8125	Intermediate Similarity	NPC91858
0.8125	Intermediate Similarity	NPC306727
0.8125	Intermediate Similarity	NPC476366
0.8095	Intermediate Similarity	NPC249423
0.809	Intermediate Similarity	NPC280149
0.809	Intermediate Similarity	NPC221111
0.8085	Intermediate Similarity	NPC115899
0.8072	Intermediate Similarity	NPC100906
0.8068	Intermediate Similarity	NPC48107
0.8068	Intermediate Similarity	NPC473229
0.8065	Intermediate Similarity	NPC316598
0.8065	Intermediate Similarity	NPC275086
0.8065	Intermediate Similarity	NPC218107
0.8065	Intermediate Similarity	NPC57079
0.8065	Intermediate Similarity	NPC478056
0.8065	Intermediate Similarity	NPC108368
0.8065	Intermediate Similarity	NPC325229
0.8049	Intermediate Similarity	NPC61952
0.8049	Intermediate Similarity	NPC470711
0.8049	Intermediate Similarity	NPC91594
0.8049	Intermediate Similarity	NPC203403
0.8049	Intermediate Similarity	NPC470758
0.8049	Intermediate Similarity	NPC283619
0.8049	Intermediate Similarity	NPC474433
0.8046	Intermediate Similarity	NPC329692
0.8046	Intermediate Similarity	NPC472985
0.8046	Intermediate Similarity	NPC472986
0.8043	Intermediate Similarity	NPC202833
0.8043	Intermediate Similarity	NPC190713
0.8022	Intermediate Similarity	NPC474690
0.8022	Intermediate Similarity	NPC299100
0.8022	Intermediate Similarity	NPC105490
0.8	Intermediate Similarity	NPC472814
0.8	Intermediate Similarity	NPC475038
0.8	Intermediate Similarity	NPC109195
0.8	Intermediate Similarity	NPC177037
0.8	Intermediate Similarity	NPC473675
0.7979	Intermediate Similarity	NPC470074
0.7979	Intermediate Similarity	NPC38855
0.7979	Intermediate Similarity	NPC266955
0.7978	Intermediate Similarity	NPC470734
0.7978	Intermediate Similarity	NPC472983
0.7978	Intermediate Similarity	NPC472973
0.7978	Intermediate Similarity	NPC170633
0.7976	Intermediate Similarity	NPC96362
0.7957	Intermediate Similarity	NPC474343
0.7957	Intermediate Similarity	NPC51499
0.7957	Intermediate Similarity	NPC141401
0.7957	Intermediate Similarity	NPC287668
0.7955	Intermediate Similarity	NPC245004
0.7952	Intermediate Similarity	NPC11908
0.7952	Intermediate Similarity	NPC239098
0.7949	Intermediate Similarity	NPC471238
0.7935	Intermediate Similarity	NPC88310
0.7935	Intermediate Similarity	NPC266899
0.7931	Intermediate Similarity	NPC474013
0.7931	Intermediate Similarity	NPC164424
0.7931	Intermediate Similarity	NPC35933
0.7931	Intermediate Similarity	NPC471267
0.7927	Intermediate Similarity	NPC470749
0.7927	Intermediate Similarity	NPC265588
0.7917	Intermediate Similarity	NPC297617
0.7917	Intermediate Similarity	NPC72151
0.7917	Intermediate Similarity	NPC471938
0.7917	Intermediate Similarity	NPC475050
0.7917	Intermediate Similarity	NPC478057
0.7912	Intermediate Similarity	NPC472641
0.7912	Intermediate Similarity	NPC472640
0.7912	Intermediate Similarity	NPC7349
0.7907	Intermediate Similarity	NPC474789
0.7907	Intermediate Similarity	NPC42476
0.7907	Intermediate Similarity	NPC243347
0.7907	Intermediate Similarity	NPC52108
0.7907	Intermediate Similarity	NPC312480
0.7901	Intermediate Similarity	NPC22134
0.7901	Intermediate Similarity	NPC243342
0.7901	Intermediate Similarity	NPC71152
0.7901	Intermediate Similarity	NPC477138
0.7895	Intermediate Similarity	NPC473160
0.7895	Intermediate Similarity	NPC115862
0.7889	Intermediate Similarity	NPC472642
0.7889	Intermediate Similarity	NPC232202
0.7882	Intermediate Similarity	NPC90055
0.7882	Intermediate Similarity	NPC473420
0.7882	Intermediate Similarity	NPC476646
0.7875	Intermediate Similarity	NPC167706
0.7875	Intermediate Similarity	NPC471272
0.7875	Intermediate Similarity	NPC477792
0.7875	Intermediate Similarity	NPC471268
0.7875	Intermediate Similarity	NPC471271
0.7872	Intermediate Similarity	NPC473154
0.7872	Intermediate Similarity	NPC278673
0.7865	Intermediate Similarity	NPC93411
0.7857	Intermediate Similarity	NPC242767
0.7857	Intermediate Similarity	NPC170394
0.7857	Intermediate Similarity	NPC308038
0.7849	Intermediate Similarity	NPC471153
0.7849	Intermediate Similarity	NPC165632
0.7848	Intermediate Similarity	NPC9942
0.7841	Intermediate Similarity	NPC322159
0.7841	Intermediate Similarity	NPC474970
0.7841	Intermediate Similarity	NPC73038
0.7841	Intermediate Similarity	NPC472974
0.7835	Intermediate Similarity	NPC471937
0.7831	Intermediate Similarity	NPC477924
0.7826	Intermediate Similarity	NPC472976
0.7826	Intermediate Similarity	NPC472977
0.7826	Intermediate Similarity	NPC469697
0.7826	Intermediate Similarity	NPC201725
0.7821	Intermediate Similarity	NPC68703
0.7821	Intermediate Similarity	NPC69649

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 NPC79945 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1333
0.2-0.3	3778
0.3-0.4	2579
0.4-0.5	839
0.5-0.6	207
0.6-0.7	217
0.7-0.8	45
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD4225	Approved
0.7802	Intermediate Similarity	NPD7515	Phase 2
0.7789	Intermediate Similarity	NPD7640	Approved
0.7789	Intermediate Similarity	NPD7639	Approved
0.7684	Intermediate Similarity	NPD7638	Approved
0.7449	Intermediate Similarity	NPD5211	Phase 2
0.7447	Intermediate Similarity	NPD7748	Approved
0.7444	Intermediate Similarity	NPD3618	Phase 1
0.7442	Intermediate Similarity	NPD7645	Phase 2
0.7419	Intermediate Similarity	NPD6079	Approved
0.7386	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD8264	Approved
0.7356	Intermediate Similarity	NPD7525	Registered
0.7347	Intermediate Similarity	NPD5344	Discontinued
0.7327	Intermediate Similarity	NPD5697	Approved
0.73	Intermediate Similarity	NPD5141	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5222	Approved
0.7255	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD6881	Approved
0.7245	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD5286	Approved
0.7245	Intermediate Similarity	NPD4696	Approved
0.7234	Intermediate Similarity	NPD7637	Suspended
0.7216	Intermediate Similarity	NPD7902	Approved
0.7216	Intermediate Similarity	NPD5173	Approved
0.7204	Intermediate Similarity	NPD5328	Approved
0.7196	Intermediate Similarity	NPD7115	Discovery
0.7184	Intermediate Similarity	NPD6013	Approved
0.7184	Intermediate Similarity	NPD6014	Approved
0.7184	Intermediate Similarity	NPD6012	Approved
0.7115	Intermediate Similarity	NPD7290	Approved
0.7115	Intermediate Similarity	NPD6883	Approved
0.7115	Intermediate Similarity	NPD7102	Approved
0.71	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD7632	Discontinued
0.71	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD5226	Approved
0.71	Intermediate Similarity	NPD5224	Approved
0.7093	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6011	Approved
0.7071	Intermediate Similarity	NPD6648	Approved
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD6675	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.7048	Intermediate Similarity	NPD6869	Approved
0.7048	Intermediate Similarity	NPD6650	Approved
0.7048	Intermediate Similarity	NPD6847	Approved
0.7048	Intermediate Similarity	NPD6649	Approved
0.7048	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD6617	Approved
0.7045	Intermediate Similarity	NPD4195	Approved
0.7045	Intermediate Similarity	NPD6929	Approved
0.7041	Intermediate Similarity	NPD4755	Approved
0.7033	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3665	Phase 1
0.7033	Intermediate Similarity	NPD3666	Approved
0.7033	Intermediate Similarity	NPD3133	Approved
0.703	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD5175	Approved
0.7	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD5223	Approved
0.699	Remote Similarity	NPD5701	Approved
0.6989	Remote Similarity	NPD3573	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.6981	Remote Similarity	NPD6882	Approved
0.6979	Remote Similarity	NPD5779	Approved
0.6979	Remote Similarity	NPD5778	Approved
0.6979	Remote Similarity	NPD4202	Approved
0.6977	Remote Similarity	NPD7339	Approved
0.6977	Remote Similarity	NPD6942	Approved
0.697	Remote Similarity	NPD5290	Discontinued
0.6966	Remote Similarity	NPD4695	Discontinued
0.6966	Remote Similarity	NPD7514	Phase 3
0.6966	Remote Similarity	NPD7332	Phase 2
0.6966	Remote Similarity	NPD6931	Approved
0.6966	Remote Similarity	NPD6930	Phase 2
0.6957	Remote Similarity	NPD1694	Approved
0.6957	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4697	Phase 3
0.6932	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7145	Approved
0.6932	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6686	Approved
0.6923	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD6695	Phase 3
0.6907	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7900	Approved
0.69	Remote Similarity	NPD4700	Approved
0.6889	Remote Similarity	NPD6902	Approved
0.6882	Remote Similarity	NPD4623	Approved
0.6882	Remote Similarity	NPD4519	Discontinued
0.6875	Remote Similarity	NPD6411	Approved
0.6869	Remote Similarity	NPD6084	Phase 2
0.6869	Remote Similarity	NPD6083	Phase 2
0.686	Remote Similarity	NPD6926	Approved
0.686	Remote Similarity	NPD6924	Approved
0.6857	Remote Similarity	NPD6373	Approved
0.6857	Remote Similarity	NPD6372	Approved
0.6848	Remote Similarity	NPD4786	Approved
0.6848	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4753	Phase 2
0.6837	Remote Similarity	NPD4629	Approved
0.6837	Remote Similarity	NPD5210	Approved
0.6824	Remote Similarity	NPD7152	Approved
0.6824	Remote Similarity	NPD7151	Approved
0.6824	Remote Similarity	NPD7150	Approved
0.6818	Remote Similarity	NPD5776	Phase 2
0.6818	Remote Similarity	NPD6925	Approved
0.6809	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6399	Phase 3
0.6778	Remote Similarity	NPD4819	Approved
0.6778	Remote Similarity	NPD4821	Approved
0.6778	Remote Similarity	NPD4820	Approved
0.6778	Remote Similarity	NPD4822	Approved
0.6774	Remote Similarity	NPD5363	Approved
0.6771	Remote Similarity	NPD5785	Approved
0.6762	Remote Similarity	NPD4730	Approved
0.6762	Remote Similarity	NPD4729	Approved
0.6759	Remote Similarity	NPD4632	Approved
0.675	Remote Similarity	NPD4192	Approved
0.675	Remote Similarity	NPD4194	Approved
0.675	Remote Similarity	NPD4193	Approved
0.675	Remote Similarity	NPD4191	Approved
0.6742	Remote Similarity	NPD4271	Approved
0.6742	Remote Similarity	NPD4268	Approved
0.6706	Remote Similarity	NPD7144	Approved
0.6706	Remote Similarity	NPD7143	Approved
0.6705	Remote Similarity	NPD6933	Approved
0.6702	Remote Similarity	NPD7521	Approved
0.6702	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7146	Approved
0.6702	Remote Similarity	NPD6684	Approved
0.6702	Remote Similarity	NPD5279	Phase 3
0.6702	Remote Similarity	NPD5330	Approved
0.6702	Remote Similarity	NPD7334	Approved
0.6702	Remote Similarity	NPD6409	Approved
0.6698	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6637	Remote Similarity	NPD7503	Approved
0.6636	Remote Similarity	NPD6868	Approved
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD5248	Approved
0.6636	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD4634	Approved
0.6636	Remote Similarity	NPD5247	Approved
0.6636	Remote Similarity	NPD6274	Approved
0.6636	Remote Similarity	NPD5251	Approved
0.6634	Remote Similarity	NPD5696	Approved
0.6632	Remote Similarity	NPD7524	Approved
0.6632	Remote Similarity	NPD7750	Discontinued
0.6629	Remote Similarity	NPD6932	Approved
0.6607	Remote Similarity	NPD7101	Approved
0.6607	Remote Similarity	NPD7100	Approved
0.6607	Remote Similarity	NPD7516	Approved
0.6604	Remote Similarity	NPD5168	Approved
0.6604	Remote Similarity	NPD5128	Approved
0.6598	Remote Similarity	NPD7838	Discovery
0.6596	Remote Similarity	NPD6893	Approved
0.6596	Remote Similarity	NPD1696	Phase 3
0.6593	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7509	Discontinued
0.6588	Remote Similarity	NPD6922	Approved
0.6588	Remote Similarity	NPD6923	Approved
0.6577	Remote Similarity	NPD6317	Approved
0.6577	Remote Similarity	NPD6009	Approved
0.6574	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5217	Approved
0.6574	Remote Similarity	NPD5215	Approved
0.6574	Remote Similarity	NPD5216	Approved
0.6571	Remote Similarity	NPD4767	Approved
0.6571	Remote Similarity	NPD4768	Approved
0.6562	Remote Similarity	NPD6903	Approved
0.6562	Remote Similarity	NPD6672	Approved
0.6562	Remote Similarity	NPD5737	Approved
0.6562	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7154	Phase 3
0.6559	Remote Similarity	NPD5362	Discontinued
0.6559	Remote Similarity	NPD5332	Approved
0.6559	Remote Similarity	NPD5331	Approved
0.6549	Remote Similarity	NPD8294	Approved
0.6549	Remote Similarity	NPD8377	Approved
0.6549	Remote Similarity	NPD6319	Approved
0.6543	Remote Similarity	NPD368	Approved
0.6538	Remote Similarity	NPD4754	Approved
0.6531	Remote Similarity	NPD5284	Approved
0.6531	Remote Similarity	NPD8035	Phase 2
0.6531	Remote Similarity	NPD8034	Phase 2
0.6531	Remote Similarity	NPD5281	Approved
0.6522	Remote Similarity	NPD6898	Phase 1
0.6522	Remote Similarity	NPD4790	Discontinued
0.6518	Remote Similarity	NPD6335	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