NPASS Compound

Structure

NPC104560 OpenBabel07101719512D 25 26 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 2.5981 -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 1.7321 0.0000 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 -5.0000 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 1.7321 -6.0000 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 2.5981 -4.5000 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 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 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 0.8660 -6.5000 0.0000 O 0 0 0 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 3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 4 7 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 19 1 0 0 0 0 11 21 1 0 0 0 0 12 20 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 1 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 20 1 1 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	373.405
LogP:	0.996
LogD:	0.798
LogS:	-3.128
# Rotatable Bonds:	7
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	4.517
Fsp3:	0.8
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:	-5.637
MDCK Permeability:	7.385089247691212e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.362
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.635
Plasma Protein Binding (PPB):	54.446022033691406%
Volume Distribution (VD):	0.457
Pgp-substrate:	43.224517822265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.228
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	5.295
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.749
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.854
Carcinogencity:	0.203
Eye Corrosion:	0.097
Eye Irritation:	0.472
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC104560

Natural Product ID:	NPC104560
*Common Name:**	4-Hydroxy-2-(2-((1R,4As,5R,6R,8As)-6-Hydroxy-5-(Hydroxymethyl)-5,8A-Dimethyl-2-Methylene-Decahydronaphthalen-1-Yl)Ethyl)But-2-Enoic Acid
IUPAC Name:	(Z)-2-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-4-hydroxybut-2-enoic acid
Synonyms:
Standard InCHIKey:	SSCXIOHKJCIXKI-KWKBPYNPSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-13-4-7-16-19(2,10-8-17(23)20(16,3)12-22)15(13)6-5-14(9-11-21)18(24)25/h9,15-17,21-23H,1,4-8,10-12H2,2-3H3,(H,24,25)/b14-9-/t15-,16+,17-,19+,20+/m1/s1
SMILES:	OC/C=C(C(=O)O)/CC[C@@H]1C(=C)CC[C@H]2[C@@]1(C)CC[C@H]([C@@]2(C)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511768
PubChem CID:	44577209
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
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	=	22420.0	nM	PMID[479361]

☑ 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 NPC104560 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	187
0.1-0.2	1017
0.2-0.3	3948
0.3-0.4	8669
0.4-0.5	13387
0.5-0.6	6916
0.6-0.7	5517
0.7-0.8	2658
0.8-0.85	320
0.85-0.9	66
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9157	High Similarity	NPC79945
0.9091	High Similarity	NPC139692
0.9024	High Similarity	NPC281880
0.9	High Similarity	NPC234993
0.9	High Similarity	NPC134072
0.9	High Similarity	NPC250757
0.9	High Similarity	NPC242848
0.9	High Similarity	NPC301534
0.8977	High Similarity	NPC472978
0.8916	High Similarity	NPC159148
0.8901	High Similarity	NPC253826
0.8837	High Similarity	NPC473226
0.8817	High Similarity	NPC282524
0.881	High Similarity	NPC2524
0.8804	High Similarity	NPC478056
0.878	High Similarity	NPC239098
0.878	High Similarity	NPC198240
0.875	High Similarity	NPC472983
0.875	High Similarity	NPC472973
0.875	High Similarity	NPC314727
0.871	High Similarity	NPC470074
0.869	High Similarity	NPC170303
0.8681	High Similarity	NPC180950
0.8681	High Similarity	NPC266899
0.8659	High Similarity	NPC474433
0.8659	High Similarity	NPC61952
0.8652	High Similarity	NPC232202
0.8636	High Similarity	NPC48107
0.8636	High Similarity	NPC473229
0.8632	High Similarity	NPC478057
0.8621	High Similarity	NPC472985
0.8621	High Similarity	NPC322159
0.8621	High Similarity	NPC472986
0.8621	High Similarity	NPC175145
0.8621	High Similarity	NPC73038
0.8621	High Similarity	NPC82979
0.8621	High Similarity	NPC475069
0.8617	High Similarity	NPC115899
0.8602	High Similarity	NPC108368
0.8602	High Similarity	NPC57079
0.8587	High Similarity	NPC202833
0.8571	High Similarity	NPC299100
0.8571	High Similarity	NPC472976
0.8571	High Similarity	NPC474690
0.8571	High Similarity	NPC472977
0.8556	High Similarity	NPC145067
0.8556	High Similarity	NPC472814
0.8556	High Similarity	NPC4036
0.8556	High Similarity	NPC233455
0.8556	High Similarity	NPC177037
0.8556	High Similarity	NPC158030
0.8556	High Similarity	NPC72845
0.8556	High Similarity	NPC65120
0.8539	High Similarity	NPC174342
0.8539	High Similarity	NPC130520
0.8539	High Similarity	NPC474704
0.8539	High Similarity	NPC293048
0.8539	High Similarity	NPC127689
0.8539	High Similarity	NPC270768
0.8539	High Similarity	NPC61543
0.8539	High Similarity	NPC262858
0.8539	High Similarity	NPC234346
0.8539	High Similarity	NPC225585
0.8539	High Similarity	NPC472240
0.8539	High Similarity	NPC475921
0.8539	High Similarity	NPC263393
0.8539	High Similarity	NPC59263
0.8539	High Similarity	NPC121798
0.8511	High Similarity	NPC266955
0.8506	High Similarity	NPC109528
0.8495	Intermediate Similarity	NPC474343
0.8488	Intermediate Similarity	NPC476927
0.8488	Intermediate Similarity	NPC243347
0.8478	Intermediate Similarity	NPC476174
0.8478	Intermediate Similarity	NPC148523
0.8478	Intermediate Similarity	NPC88310
0.8478	Intermediate Similarity	NPC53565
0.8471	Intermediate Similarity	NPC473420
0.8471	Intermediate Similarity	NPC90055
0.8471	Intermediate Similarity	NPC40228
0.8462	Intermediate Similarity	NPC214756
0.8462	Intermediate Similarity	NPC476304
0.8462	Intermediate Similarity	NPC472871
0.8462	Intermediate Similarity	NPC295643
0.8462	Intermediate Similarity	NPC272075
0.8452	Intermediate Similarity	NPC308038
0.8444	Intermediate Similarity	NPC78973
0.8444	Intermediate Similarity	NPC470589
0.8444	Intermediate Similarity	NPC130278
0.8444	Intermediate Similarity	NPC126369
0.8444	Intermediate Similarity	NPC111110
0.8438	Intermediate Similarity	NPC95899
0.8438	Intermediate Similarity	NPC112009
0.8438	Intermediate Similarity	NPC72151
0.8438	Intermediate Similarity	NPC475050
0.8427	Intermediate Similarity	NPC52169
0.8427	Intermediate Similarity	NPC182797
0.8427	Intermediate Similarity	NPC472870
0.8421	Intermediate Similarity	NPC118174
0.8421	Intermediate Similarity	NPC115862
0.8421	Intermediate Similarity	NPC303559
0.8421	Intermediate Similarity	NPC471412
0.8409	Intermediate Similarity	NPC131813
0.8409	Intermediate Similarity	NPC472974
0.8409	Intermediate Similarity	NPC325594
0.8409	Intermediate Similarity	NPC472869
0.8404	Intermediate Similarity	NPC316598
0.8391	Intermediate Similarity	NPC130966
0.8391	Intermediate Similarity	NPC19849
0.8391	Intermediate Similarity	NPC472864
0.8391	Intermediate Similarity	NPC476412
0.8387	Intermediate Similarity	NPC471153
0.8387	Intermediate Similarity	NPC114743
0.8387	Intermediate Similarity	NPC195366
0.8387	Intermediate Similarity	NPC472806
0.8387	Intermediate Similarity	NPC98874
0.8387	Intermediate Similarity	NPC472941
0.8387	Intermediate Similarity	NPC167193
0.8387	Intermediate Similarity	NPC456
0.8387	Intermediate Similarity	NPC116457
0.8372	Intermediate Similarity	NPC93590
0.8372	Intermediate Similarity	NPC256112
0.837	Intermediate Similarity	NPC91010
0.837	Intermediate Similarity	NPC119562
0.837	Intermediate Similarity	NPC470958
0.837	Intermediate Similarity	NPC57117
0.837	Intermediate Similarity	NPC279410
0.837	Intermediate Similarity	NPC476186
0.837	Intermediate Similarity	NPC469406
0.837	Intermediate Similarity	NPC470957
0.8353	Intermediate Similarity	NPC271104
0.8352	Intermediate Similarity	NPC473998
0.8352	Intermediate Similarity	NPC282616
0.8352	Intermediate Similarity	NPC228784
0.8352	Intermediate Similarity	NPC110923
0.8352	Intermediate Similarity	NPC74296
0.8352	Intermediate Similarity	NPC155120
0.8352	Intermediate Similarity	NPC324341
0.8352	Intermediate Similarity	NPC472975
0.8352	Intermediate Similarity	NPC966
0.8352	Intermediate Similarity	NPC288833
0.8333	Intermediate Similarity	NPC198664
0.8333	Intermediate Similarity	NPC293753
0.8333	Intermediate Similarity	NPC114540
0.8333	Intermediate Similarity	NPC476949
0.8333	Intermediate Similarity	NPC32577
0.8333	Intermediate Similarity	NPC146554
0.8333	Intermediate Similarity	NPC281524
0.8333	Intermediate Similarity	NPC59436
0.8333	Intermediate Similarity	NPC25906
0.8333	Intermediate Similarity	NPC143232
0.8333	Intermediate Similarity	NPC50488
0.8333	Intermediate Similarity	NPC214387
0.8333	Intermediate Similarity	NPC476081
0.8333	Intermediate Similarity	NPC64872
0.8333	Intermediate Similarity	NPC320447
0.8333	Intermediate Similarity	NPC309603
0.8333	Intermediate Similarity	NPC290972
0.8333	Intermediate Similarity	NPC155332
0.8333	Intermediate Similarity	NPC136289
0.8333	Intermediate Similarity	NPC473999
0.8333	Intermediate Similarity	NPC274330
0.8333	Intermediate Similarity	NPC474396
0.8316	Intermediate Similarity	NPC201406
0.8316	Intermediate Similarity	NPC476274
0.8316	Intermediate Similarity	NPC474012
0.8316	Intermediate Similarity	NPC471413
0.8316	Intermediate Similarity	NPC476299
0.8316	Intermediate Similarity	NPC471041
0.8315	Intermediate Similarity	NPC477926
0.8315	Intermediate Similarity	NPC242468
0.8315	Intermediate Similarity	NPC142361
0.8315	Intermediate Similarity	NPC102683
0.8315	Intermediate Similarity	NPC142415
0.8315	Intermediate Similarity	NPC51700
0.8315	Intermediate Similarity	NPC171203
0.8315	Intermediate Similarity	NPC18064
0.8315	Intermediate Similarity	NPC476409
0.8315	Intermediate Similarity	NPC307426
0.8315	Intermediate Similarity	NPC98442
0.8315	Intermediate Similarity	NPC68160
0.8315	Intermediate Similarity	NPC293564
0.8315	Intermediate Similarity	NPC130577
0.8315	Intermediate Similarity	NPC88716
0.8315	Intermediate Similarity	NPC474684
0.8298	Intermediate Similarity	NPC474938
0.8298	Intermediate Similarity	NPC156546
0.8298	Intermediate Similarity	NPC108078
0.8298	Intermediate Similarity	NPC320306
0.8298	Intermediate Similarity	NPC89225
0.8298	Intermediate Similarity	NPC73911
0.8298	Intermediate Similarity	NPC474785
0.8298	Intermediate Similarity	NPC475709
0.8298	Intermediate Similarity	NPC472851
0.8295	Intermediate Similarity	NPC470574
0.8295	Intermediate Similarity	NPC65661
0.8295	Intermediate Similarity	NPC471344
0.8295	Intermediate Similarity	NPC86316
0.8295	Intermediate Similarity	NPC106416
0.8295	Intermediate Similarity	NPC52628

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 NPC104560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1392
0.2-0.3	3529
0.3-0.4	2560
0.4-0.5	987
0.5-0.6	221
0.6-0.7	200
0.7-0.8	96
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8556	High Similarity	NPD7515	Phase 2
0.8211	Intermediate Similarity	NPD4225	Approved
0.8172	Intermediate Similarity	NPD7748	Approved
0.8125	Intermediate Similarity	NPD7639	Approved
0.8125	Intermediate Similarity	NPD7640	Approved
0.8021	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD3618	Phase 1
0.7957	Intermediate Similarity	NPD6079	Approved
0.7955	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD5328	Approved
0.7917	Intermediate Similarity	NPD7902	Approved
0.7778	Intermediate Similarity	NPD5211	Phase 2
0.7745	Intermediate Similarity	NPD6881	Approved
0.7745	Intermediate Similarity	NPD6899	Approved
0.7723	Intermediate Similarity	NPD6675	Approved
0.7723	Intermediate Similarity	NPD7128	Approved
0.7723	Intermediate Similarity	NPD6402	Approved
0.7723	Intermediate Similarity	NPD5739	Approved
0.7692	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD7115	Discovery
0.7647	Intermediate Similarity	NPD5697	Approved
0.7629	Intermediate Similarity	NPD5222	Approved
0.7629	Intermediate Similarity	NPD5221	Approved
0.7629	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5141	Approved
0.7604	Intermediate Similarity	NPD7900	Approved
0.7604	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7290	Approved
0.7596	Intermediate Similarity	NPD7102	Approved
0.7596	Intermediate Similarity	NPD6883	Approved
0.7582	Intermediate Similarity	NPD3666	Approved
0.7582	Intermediate Similarity	NPD3133	Approved
0.7582	Intermediate Similarity	NPD3665	Phase 1
0.7582	Intermediate Similarity	NPD4786	Approved
0.7576	Intermediate Similarity	NPD5286	Approved
0.7576	Intermediate Similarity	NPD4696	Approved
0.7576	Intermediate Similarity	NPD5285	Approved
0.7573	Intermediate Similarity	NPD6686	Approved
0.7573	Intermediate Similarity	NPD7320	Approved
0.7556	Intermediate Similarity	NPD3667	Approved
0.7551	Intermediate Similarity	NPD6083	Phase 2
0.7551	Intermediate Similarity	NPD6084	Phase 2
0.7551	Intermediate Similarity	NPD4755	Approved
0.7551	Intermediate Similarity	NPD5173	Approved
0.7528	Intermediate Similarity	NPD4695	Discontinued
0.7524	Intermediate Similarity	NPD8130	Phase 1
0.7524	Intermediate Similarity	NPD6617	Approved
0.7524	Intermediate Similarity	NPD6650	Approved
0.7524	Intermediate Similarity	NPD6869	Approved
0.7524	Intermediate Similarity	NPD6649	Approved
0.7524	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD5778	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD6014	Approved
0.7476	Intermediate Similarity	NPD5701	Approved
0.7453	Intermediate Similarity	NPD8297	Approved
0.7453	Intermediate Similarity	NPD6882	Approved
0.7449	Intermediate Similarity	NPD4697	Phase 3
0.7426	Intermediate Similarity	NPD4633	Approved
0.7426	Intermediate Similarity	NPD5225	Approved
0.7426	Intermediate Similarity	NPD5224	Approved
0.7426	Intermediate Similarity	NPD5226	Approved
0.7426	Intermediate Similarity	NPD7632	Discontinued
0.7419	Intermediate Similarity	NPD7334	Approved
0.7419	Intermediate Similarity	NPD7521	Approved
0.7419	Intermediate Similarity	NPD6684	Approved
0.7419	Intermediate Similarity	NPD5330	Approved
0.7419	Intermediate Similarity	NPD6409	Approved
0.7419	Intermediate Similarity	NPD7146	Approved
0.7404	Intermediate Similarity	NPD6011	Approved
0.74	Intermediate Similarity	NPD4700	Approved
0.7396	Intermediate Similarity	NPD6411	Approved
0.7368	Intermediate Similarity	NPD4753	Phase 2
0.7353	Intermediate Similarity	NPD5174	Approved
0.7353	Intermediate Similarity	NPD5175	Approved
0.734	Intermediate Similarity	NPD3573	Approved
0.7327	Intermediate Similarity	NPD5223	Approved
0.7312	Intermediate Similarity	NPD5363	Approved
0.7312	Intermediate Similarity	NPD1694	Approved
0.7292	Intermediate Similarity	NPD5785	Approved
0.7263	Intermediate Similarity	NPD5737	Approved
0.7263	Intermediate Similarity	NPD6672	Approved
0.7263	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6903	Approved
0.7234	Intermediate Similarity	NPD4623	Approved
0.7234	Intermediate Similarity	NPD5279	Phase 3
0.7234	Intermediate Similarity	NPD4519	Discontinued
0.7234	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.7216	Intermediate Similarity	NPD7637	Suspended
0.7216	Intermediate Similarity	NPD8034	Phase 2
0.7216	Intermediate Similarity	NPD8035	Phase 2
0.7196	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6101	Approved
0.7188	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4629	Approved
0.7172	Intermediate Similarity	NPD5695	Phase 3
0.7172	Intermediate Similarity	NPD5210	Approved
0.717	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7525	Registered
0.7129	Intermediate Similarity	NPD5696	Approved
0.7097	Intermediate Similarity	NPD7154	Phase 3
0.7097	Intermediate Similarity	NPD5362	Discontinued
0.7091	Intermediate Similarity	NPD6274	Approved
0.7091	Intermediate Similarity	NPD6868	Approved
0.7079	Intermediate Similarity	NPD6117	Approved
0.7075	Intermediate Similarity	NPD5128	Approved
0.7075	Intermediate Similarity	NPD4729	Approved
0.7075	Intermediate Similarity	NPD4730	Approved
0.7064	Intermediate Similarity	NPD4632	Approved
0.7054	Intermediate Similarity	NPD7100	Approved
0.7054	Intermediate Similarity	NPD7101	Approved
0.7048	Intermediate Similarity	NPD4768	Approved
0.7048	Intermediate Similarity	NPD4767	Approved
0.7021	Intermediate Similarity	NPD3668	Phase 3
0.7019	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5344	Discontinued
0.6989	Remote Similarity	NPD4223	Phase 3
0.6989	Remote Similarity	NPD4221	Approved
0.6989	Remote Similarity	NPD4270	Approved
0.6989	Remote Similarity	NPD4269	Approved
0.6966	Remote Similarity	NPD8264	Approved
0.6964	Remote Similarity	NPD6335	Approved
0.6957	Remote Similarity	NPD4821	Approved
0.6957	Remote Similarity	NPD4820	Approved
0.6957	Remote Similarity	NPD4819	Approved
0.6957	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4822	Approved
0.6947	Remote Similarity	NPD5329	Approved
0.6944	Remote Similarity	NPD5250	Approved
0.6944	Remote Similarity	NPD5251	Approved
0.6944	Remote Similarity	NPD5249	Phase 3
0.6944	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4634	Approved
0.6944	Remote Similarity	NPD5247	Approved
0.6944	Remote Similarity	NPD5248	Approved
0.6939	Remote Similarity	NPD46	Approved
0.6939	Remote Similarity	NPD6698	Approved
0.6931	Remote Similarity	NPD7614	Phase 1
0.6923	Remote Similarity	NPD6697	Approved
0.6923	Remote Similarity	NPD4271	Approved
0.6923	Remote Similarity	NPD6118	Approved
0.6923	Remote Similarity	NPD4268	Approved
0.6923	Remote Similarity	NPD6115	Approved
0.6923	Remote Similarity	NPD6114	Approved
0.6916	Remote Similarity	NPD5168	Approved
0.6915	Remote Similarity	NPD4788	Approved
0.6893	Remote Similarity	NPD6404	Discontinued
0.6881	Remote Similarity	NPD5215	Approved
0.6881	Remote Similarity	NPD5217	Approved
0.6881	Remote Similarity	NPD5216	Approved
0.6875	Remote Similarity	NPD6317	Approved
0.6875	Remote Similarity	NPD6009	Approved
0.6869	Remote Similarity	NPD5281	Approved
0.6869	Remote Similarity	NPD5284	Approved
0.6854	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6929	Approved
0.6842	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6319	Approved
0.6842	Remote Similarity	NPD4197	Approved
0.6838	Remote Similarity	NPD7507	Approved
0.6837	Remote Similarity	NPD6080	Approved
0.6837	Remote Similarity	NPD6904	Approved
0.6837	Remote Similarity	NPD6673	Approved
0.6832	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6412	Phase 2
0.6814	Remote Similarity	NPD6313	Approved
0.6814	Remote Similarity	NPD6314	Approved
0.6789	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5169	Approved
0.6789	Remote Similarity	NPD5135	Approved
0.6783	Remote Similarity	NPD6909	Approved
0.6783	Remote Similarity	NPD6908	Approved
0.6778	Remote Similarity	NPD6942	Approved
0.6778	Remote Similarity	NPD7339	Approved
0.6774	Remote Similarity	NPD6931	Approved
0.6774	Remote Similarity	NPD5368	Approved
0.6774	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6930	Phase 2
0.6774	Remote Similarity	NPD4252	Approved
0.6771	Remote Similarity	NPD1696	Phase 3
0.6752	Remote Similarity	NPD7492	Approved
0.6739	Remote Similarity	NPD3617	Approved
0.6737	Remote Similarity	NPD5332	Approved
0.6737	Remote Similarity	NPD5331	Approved
0.6737	Remote Similarity	NPD6695	Phase 3
0.6731	Remote Similarity	NPD6648	Approved
0.6729	Remote Similarity	NPD6008	Approved
0.6727	Remote Similarity	NPD5127	Approved
0.6703	Remote Similarity	NPD3701	Clinical (unspecified phase)

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