NPASS Compound

Structure

NPC234993 OpenBabel07101718272D 25 27 0 0 1 0 0 0 0 0999 V2000 2.4487 3.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4128 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 0.8364 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 5.0468 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9128 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 2.3364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1808 3.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0468 2.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9128 0.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 1.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9128 1.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4128 2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 4.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 0.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 4 5 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 8 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 19 1 0 0 0 0 9 25 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 6 0 0 0 15 22 1 6 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 20 1 6 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 6 0 0 0 20 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.21
Volume:	364.849
LogP:	1.717
LogD:	1.568
LogS:	-3.057
# Rotatable Bonds:	4
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	4.712
Fsp3:	0.7
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:	-5.397
MDCK Permeability:	4.623764198186109e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.815
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.262

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.567
Plasma Protein Binding (PPB):	73.21357727050781%
Volume Distribution (VD):	2.995
Pgp-substrate:	26.419527053833008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	8.396
Half-life (T1/2):	0.654

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.29
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.318
Carcinogencity:	0.419
Eye Corrosion:	0.018
Eye Irritation:	0.087
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC234993

Natural Product ID:	NPC234993
*Common Name:**	7R-Hydroxy-14-Deoxyandrographolide
IUPAC Name:	4-[2-[(1S,3R,4aS,5R,6R,8aS)-3,6-dihydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	KNCLIXUHDVRNQB-UQZPWQSVSA-N
Standard InCHI:	InChI=1S/C20H30O5/c1-12-14(5-4-13-7-9-25-18(13)24)19(2)8-6-17(23)20(3,11-21)16(19)10-15(12)22/h7,14-17,21-23H,1,4-6,8-11H2,2-3H3/t14-,15-,16+,17-,19+,20+/m1/s1
SMILES:	OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1C[C@@H](O)C(=C)[C@H]2CCC1=CCOC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466745
PubChem CID:	24879275
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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	=	22480.0	nM	PMID[569196]

☑ 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 NPC234993 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	190
0.1-0.2	1079
0.2-0.3	3606
0.3-0.4	6477
0.4-0.5	14239
0.5-0.6	7065
0.6-0.7	6461
0.7-0.8	3175
0.8-0.85	301
0.85-0.9	81
0.9-0.95	19
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC134072
0.9663	High Similarity	NPC139692
0.956	High Similarity	NPC242848
0.9158	High Similarity	NPC471412
0.914	High Similarity	NPC202833
0.913	High Similarity	NPC57117
0.9121	High Similarity	NPC472814
0.9121	High Similarity	NPC177037
0.9062	High Similarity	NPC476081
0.9053	High Similarity	NPC471413
0.9	High Similarity	NPC104560
0.8989	High Similarity	NPC131813
0.8969	High Similarity	NPC120321
0.8913	High Similarity	NPC72845
0.8901	High Similarity	NPC174342
0.8889	High Similarity	NPC187435
0.8889	High Similarity	NPC67321
0.8876	High Similarity	NPC65661
0.8876	High Similarity	NPC86316
0.8876	High Similarity	NPC106416
0.8866	High Similarity	NPC162973
0.8854	High Similarity	NPC474012
0.8854	High Similarity	NPC47024
0.8854	High Similarity	NPC476767
0.8854	High Similarity	NPC476299
0.8842	High Similarity	NPC253826
0.8842	High Similarity	NPC474343
0.8842	High Similarity	NPC475709
0.8817	High Similarity	NPC205034
0.8817	High Similarity	NPC152778
0.8817	High Similarity	NPC162615
0.8817	High Similarity	NPC115021
0.8804	High Similarity	NPC51486
0.8804	High Similarity	NPC78973
0.88	High Similarity	NPC306265
0.8788	High Similarity	NPC34768
0.8776	High Similarity	NPC112009
0.8763	High Similarity	NPC303559
0.8737	High Similarity	NPC29952
0.871	High Similarity	NPC477783
0.87	High Similarity	NPC179380
0.8696	High Similarity	NPC474396
0.8696	High Similarity	NPC5509
0.8696	High Similarity	NPC50488
0.8673	High Similarity	NPC58329
0.8673	High Similarity	NPC109195
0.8673	High Similarity	NPC475038
0.866	High Similarity	NPC251680
0.866	High Similarity	NPC201406
0.866	High Similarity	NPC117685
0.8652	High Similarity	NPC311070
0.8632	High Similarity	NPC276110
0.8632	High Similarity	NPC183012
0.8617	High Similarity	NPC472303
0.8617	High Similarity	NPC472640
0.8617	High Similarity	NPC472641
0.8617	High Similarity	NPC472812
0.8602	High Similarity	NPC472642
0.8602	High Similarity	NPC477782
0.8602	High Similarity	NPC310479
0.8602	High Similarity	NPC232202
0.8602	High Similarity	NPC182136
0.8586	High Similarity	NPC478057
0.8586	High Similarity	NPC180204
0.8586	High Similarity	NPC471938
0.8557	High Similarity	NPC325229
0.8557	High Similarity	NPC57079
0.8557	High Similarity	NPC159763
0.8557	High Similarity	NPC275086
0.8557	High Similarity	NPC108368
0.8557	High Similarity	NPC316598
0.8557	High Similarity	NPC124512
0.8557	High Similarity	NPC216478
0.8557	High Similarity	NPC278386
0.8542	High Similarity	NPC473153
0.8542	High Similarity	NPC165632
0.8542	High Similarity	NPC16967
0.8539	High Similarity	NPC200513
0.8526	High Similarity	NPC24861
0.8526	High Similarity	NPC105490
0.8526	High Similarity	NPC191521
0.8515	High Similarity	NPC302788
0.8511	High Similarity	NPC473944
0.8511	High Similarity	NPC289479
0.8511	High Similarity	NPC472811
0.85	High Similarity	NPC471937
0.8495	Intermediate Similarity	NPC251528
0.8485	Intermediate Similarity	NPC165250
0.8485	Intermediate Similarity	NPC114540
0.8485	Intermediate Similarity	NPC295791
0.8485	Intermediate Similarity	NPC471914
0.8485	Intermediate Similarity	NPC32577
0.8485	Intermediate Similarity	NPC155332
0.8478	Intermediate Similarity	NPC312561
0.8469	Intermediate Similarity	NPC471041
0.8469	Intermediate Similarity	NPC470074
0.8469	Intermediate Similarity	NPC38855
0.8469	Intermediate Similarity	NPC16601
0.8469	Intermediate Similarity	NPC306856
0.8462	Intermediate Similarity	NPC470063
0.8454	Intermediate Similarity	NPC287668
0.8454	Intermediate Similarity	NPC51499
0.8454	Intermediate Similarity	NPC73911
0.8447	Intermediate Similarity	NPC179642
0.8444	Intermediate Similarity	NPC79945
0.8438	Intermediate Similarity	NPC259042
0.8438	Intermediate Similarity	NPC157686
0.8438	Intermediate Similarity	NPC209355
0.8431	Intermediate Similarity	NPC275539
0.8431	Intermediate Similarity	NPC189075
0.8431	Intermediate Similarity	NPC476765
0.8421	Intermediate Similarity	NPC53555
0.8421	Intermediate Similarity	NPC7349
0.8421	Intermediate Similarity	NPC472871
0.8416	Intermediate Similarity	NPC266570
0.8404	Intermediate Similarity	NPC232426
0.8404	Intermediate Similarity	NPC221111
0.8404	Intermediate Similarity	NPC281942
0.8404	Intermediate Similarity	NPC158488
0.8404	Intermediate Similarity	NPC280149
0.84	Intermediate Similarity	NPC471208
0.84	Intermediate Similarity	NPC476237
0.84	Intermediate Similarity	NPC95899
0.84	Intermediate Similarity	NPC159533
0.8387	Intermediate Similarity	NPC472810
0.8387	Intermediate Similarity	NPC472809
0.8384	Intermediate Similarity	NPC115899
0.837	Intermediate Similarity	NPC329692
0.837	Intermediate Similarity	NPC472985
0.837	Intermediate Similarity	NPC472986
0.8367	Intermediate Similarity	NPC278673
0.8367	Intermediate Similarity	NPC478056
0.8367	Intermediate Similarity	NPC218107
0.8367	Intermediate Similarity	NPC23364
0.8367	Intermediate Similarity	NPC474440
0.8352	Intermediate Similarity	NPC32223
0.8351	Intermediate Similarity	NPC284518
0.8351	Intermediate Similarity	NPC301534
0.8351	Intermediate Similarity	NPC250757
0.835	Intermediate Similarity	NPC474243
0.8333	Intermediate Similarity	NPC225474
0.8333	Intermediate Similarity	NPC474554
0.8333	Intermediate Similarity	NPC110496
0.8333	Intermediate Similarity	NPC469596
0.8333	Intermediate Similarity	NPC148000
0.8316	Intermediate Similarity	NPC141831
0.8316	Intermediate Similarity	NPC329842
0.8316	Intermediate Similarity	NPC78594
0.8316	Intermediate Similarity	NPC186363
0.8316	Intermediate Similarity	NPC233345
0.83	Intermediate Similarity	NPC472815
0.83	Intermediate Similarity	NPC273005
0.83	Intermediate Similarity	NPC31058
0.83	Intermediate Similarity	NPC469606
0.83	Intermediate Similarity	NPC476769
0.8298	Intermediate Similarity	NPC116620
0.8298	Intermediate Similarity	NPC314727
0.8286	Intermediate Similarity	NPC90952
0.8283	Intermediate Similarity	NPC324841
0.8283	Intermediate Similarity	NPC473219
0.8283	Intermediate Similarity	NPC470761
0.8283	Intermediate Similarity	NPC472644
0.8283	Intermediate Similarity	NPC266955
0.828	Intermediate Similarity	NPC166857
0.828	Intermediate Similarity	NPC181103
0.8269	Intermediate Similarity	NPC472666
0.8269	Intermediate Similarity	NPC476766
0.8265	Intermediate Similarity	NPC473963
0.8265	Intermediate Similarity	NPC132753
0.8265	Intermediate Similarity	NPC121402
0.8265	Intermediate Similarity	NPC151681
0.8265	Intermediate Similarity	NPC91695
0.8265	Intermediate Similarity	NPC175351
0.8265	Intermediate Similarity	NPC70145
0.8265	Intermediate Similarity	NPC53844
0.8265	Intermediate Similarity	NPC224356
0.8261	Intermediate Similarity	NPC189311
0.8261	Intermediate Similarity	NPC52628
0.8252	Intermediate Similarity	NPC90946
0.8252	Intermediate Similarity	NPC392
0.8252	Intermediate Similarity	NPC219900
0.8252	Intermediate Similarity	NPC300614
0.8252	Intermediate Similarity	NPC473483
0.8252	Intermediate Similarity	NPC177524
0.8252	Intermediate Similarity	NPC325054
0.8252	Intermediate Similarity	NPC472825
0.8247	Intermediate Similarity	NPC471915
0.8247	Intermediate Similarity	NPC472441
0.8247	Intermediate Similarity	NPC111273
0.8247	Intermediate Similarity	NPC266899
0.8235	Intermediate Similarity	NPC478208
0.8235	Intermediate Similarity	NPC469607
0.8235	Intermediate Similarity	NPC111952
0.8229	Intermediate Similarity	NPC475657
0.8229	Intermediate Similarity	NPC110022
0.8224	Intermediate Similarity	NPC471816
0.8222	Intermediate Similarity	NPC170303
0.8222	Intermediate Similarity	NPC40228
0.8222	Intermediate Similarity	NPC14203
0.8222	Intermediate Similarity	NPC229584

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 NPC234993 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	1364
0.2-0.3	3418
0.3-0.4	2573
0.4-0.5	1065
0.5-0.6	278
0.6-0.7	202
0.7-0.8	84
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.866	High Similarity	NPD7640	Approved
0.866	High Similarity	NPD7639	Approved
0.8557	High Similarity	NPD4225	Approved
0.8557	High Similarity	NPD7638	Approved
0.8539	High Similarity	NPD4752	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD6686	Approved
0.8	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7632	Discontinued
0.7818	Intermediate Similarity	NPD7115	Discovery
0.7778	Intermediate Similarity	NPD7748	Approved
0.7757	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7515	Phase 2
0.7684	Intermediate Similarity	NPD1694	Approved
0.7642	Intermediate Similarity	NPD5697	Approved
0.7604	Intermediate Similarity	NPD3618	Phase 1
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.7549	Intermediate Similarity	NPD7902	Approved
0.7547	Intermediate Similarity	NPD5739	Approved
0.7547	Intermediate Similarity	NPD6675	Approved
0.7547	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD5778	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD5701	Approved
0.7477	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7507	Approved
0.7431	Intermediate Similarity	NPD6883	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7431	Intermediate Similarity	NPD7102	Approved
0.7429	Intermediate Similarity	NPD5211	Phase 2
0.7407	Intermediate Similarity	NPD6011	Approved
0.7407	Intermediate Similarity	NPD7320	Approved
0.74	Intermediate Similarity	NPD6079	Approved
0.74	Intermediate Similarity	NPD7637	Suspended
0.7379	Intermediate Similarity	NPD6084	Phase 2
0.7379	Intermediate Similarity	NPD6083	Phase 2
0.7374	Intermediate Similarity	NPD5328	Approved
0.7364	Intermediate Similarity	NPD6649	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.7364	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6617	Approved
0.7364	Intermediate Similarity	NPD6650	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7333	Intermediate Similarity	NPD5344	Discontinued
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.73	Intermediate Similarity	NPD6698	Approved
0.73	Intermediate Similarity	NPD5785	Approved
0.73	Intermediate Similarity	NPD46	Approved
0.7297	Intermediate Similarity	NPD8297	Approved
0.7297	Intermediate Similarity	NPD6882	Approved
0.729	Intermediate Similarity	NPD5141	Approved
0.7282	Intermediate Similarity	NPD5222	Approved
0.7282	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5221	Approved
0.7255	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7900	Approved
0.725	Intermediate Similarity	NPD7319	Approved
0.7245	Intermediate Similarity	NPD7334	Approved
0.7245	Intermediate Similarity	NPD6684	Approved
0.7245	Intermediate Similarity	NPD7521	Approved
0.7245	Intermediate Similarity	NPD7146	Approved
0.7245	Intermediate Similarity	NPD6409	Approved
0.7245	Intermediate Similarity	NPD5330	Approved
0.7238	Intermediate Similarity	NPD4696	Approved
0.7238	Intermediate Similarity	NPD5285	Approved
0.7238	Intermediate Similarity	NPD5286	Approved
0.7232	Intermediate Similarity	NPD4632	Approved
0.7216	Intermediate Similarity	NPD3665	Phase 1
0.7216	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3666	Approved
0.7216	Intermediate Similarity	NPD3133	Approved
0.7212	Intermediate Similarity	NPD4755	Approved
0.7212	Intermediate Similarity	NPD5173	Approved
0.7188	Intermediate Similarity	NPD3667	Approved
0.7184	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5695	Phase 3
0.7172	Intermediate Similarity	NPD3573	Approved
0.7157	Intermediate Similarity	NPD4202	Approved
0.7155	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7328	Approved
0.713	Intermediate Similarity	NPD7327	Approved
0.7117	Intermediate Similarity	NPD6371	Approved
0.7115	Intermediate Similarity	NPD4697	Phase 3
0.7105	Intermediate Similarity	NPD6274	Approved
0.7103	Intermediate Similarity	NPD5224	Approved
0.7103	Intermediate Similarity	NPD5225	Approved
0.7103	Intermediate Similarity	NPD5226	Approved
0.7103	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD6903	Approved
0.71	Intermediate Similarity	NPD6672	Approved
0.71	Intermediate Similarity	NPD5737	Approved
0.71	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4700	Approved
0.7075	Intermediate Similarity	NPD6648	Approved
0.7069	Intermediate Similarity	NPD7516	Approved
0.7064	Intermediate Similarity	NPD6008	Approved
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD8035	Phase 2
0.7059	Intermediate Similarity	NPD6411	Approved
0.7059	Intermediate Similarity	NPD8034	Phase 2
0.7054	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6009	Approved
0.7041	Intermediate Similarity	NPD4786	Approved
0.7037	Intermediate Similarity	NPD5175	Approved
0.7037	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD4753	Phase 2
0.7009	Intermediate Similarity	NPD8377	Approved
0.7009	Intermediate Similarity	NPD8294	Approved
0.7009	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD6412	Phase 2
0.6991	Remote Similarity	NPD6053	Discontinued
0.6979	Remote Similarity	NPD4695	Discontinued
0.6964	Remote Similarity	NPD4634	Approved
0.6957	Remote Similarity	NPD6868	Approved
0.6949	Remote Similarity	NPD8033	Approved
0.6949	Remote Similarity	NPD8378	Approved
0.6949	Remote Similarity	NPD8335	Approved
0.6949	Remote Similarity	NPD8380	Approved
0.6949	Remote Similarity	NPD5983	Phase 2
0.6949	Remote Similarity	NPD8379	Approved
0.6949	Remote Similarity	NPD8296	Approved
0.6947	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7154	Phase 3
0.6939	Remote Similarity	NPD6695	Phase 3
0.6937	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.69	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5279	Phase 3
0.69	Remote Similarity	NPD4519	Discontinued
0.69	Remote Similarity	NPD4623	Approved
0.6897	Remote Similarity	NPD6317	Approved
0.6869	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6054	Approved
0.6863	Remote Similarity	NPD6101	Approved
0.6863	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6616	Approved
0.6857	Remote Similarity	NPD5210	Approved
0.6857	Remote Similarity	NPD4629	Approved
0.6857	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6313	Approved
0.6838	Remote Similarity	NPD6314	Approved
0.6838	Remote Similarity	NPD6335	Approved
0.6833	Remote Similarity	NPD7604	Phase 2
0.6807	Remote Similarity	NPD6016	Approved
0.6807	Remote Similarity	NPD7503	Approved
0.6807	Remote Similarity	NPD6015	Approved
0.6803	Remote Similarity	NPD7078	Approved
0.68	Remote Similarity	NPD5363	Approved
0.6796	Remote Similarity	NPD7838	Discovery
0.6786	Remote Similarity	NPD4730	Approved
0.6786	Remote Similarity	NPD4729	Approved
0.6786	Remote Similarity	NPD5128	Approved
0.6783	Remote Similarity	NPD8133	Approved
0.6771	Remote Similarity	NPD6118	Approved
0.6771	Remote Similarity	NPD6114	Approved
0.6771	Remote Similarity	NPD6115	Approved
0.6771	Remote Similarity	NPD6697	Approved
0.6768	Remote Similarity	NPD5362	Discontinued
0.6757	Remote Similarity	NPD4768	Approved
0.6757	Remote Similarity	NPD4767	Approved
0.675	Remote Similarity	NPD5988	Approved
0.675	Remote Similarity	NPD6370	Approved
0.6748	Remote Similarity	NPD7736	Approved
0.6727	Remote Similarity	NPD4754	Approved
0.6726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6059	Approved
0.6721	Remote Similarity	NPD6336	Discontinued
0.6701	Remote Similarity	NPD7645	Phase 2
0.6701	Remote Similarity	NPD6929	Approved
0.67	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD6080	Approved
0.6699	Remote Similarity	NPD6051	Approved
0.6699	Remote Similarity	NPD6673	Approved
0.6699	Remote Similarity	NPD6904	Approved
0.6696	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD7524	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