NPASS Compound

Structure

NPC176845 OpenBabel07101718322D 29 32 0 0 1 0 0 0 0 0999 V2000 -1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2232 3.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8709 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5630 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1133 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4702 2.6351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2650 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0896 0.9960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 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 2.9793 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4762 2.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8885 1.7907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1133 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 17 1 0 0 0 0 10 19 2 0 0 0 0 12 18 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 25 2 0 0 0 0 14 28 1 0 0 0 0 15 26 2 0 0 0 0 15 29 1 0 0 0 0 16 11 1 1 0 0 0 16 17 1 0 0 0 0 17 27 2 0 0 0 0 18 20 1 0 0 0 0 18 28 1 1 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 1 0 0 0 21 24 1 1 0 0 0 21 29 1 0 0 0 0 23 6 1 1 0 0 0 24 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.22
Volume:	420.203
LogP:	3.772
LogD:	2.936
LogS:	-4.742
# Rotatable Bonds:	4
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.638
Synthetic Accessibility Score:	5.881
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.039
MDCK Permeability:	2.575290454842616e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.537
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.801
Plasma Protein Binding (PPB):	78.22455596923828%
Volume Distribution (VD):	0.756
Pgp-substrate:	28.754425048828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.43
CYP3A4-substrate:	0.891

ADMET: Excretion

Clearance (CL):	2.479
Half-life (T1/2):	0.476

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.29
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.122
Maximum Recommended Daily Dose:	0.072
Skin Sensitization:	0.141
Carcinogencity:	0.7
Eye Corrosion:	0.825
Eye Irritation:	0.141
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC176845

Natural Product ID:	NPC176845
*Common Name:**	STKAPMLMWWTKPK-FBCMHIKGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	STKAPMLMWWTKPK-FBCMHIKGSA-N
Standard InCHI:	InChI=1S/C24H32O5/c1-13-16-11-24(21(13)29-15(3)26)12-18(28-14(2)25)20-22(4,5)8-7-9-23(20,6)19(24)10-17(16)27/h10,16,18,20-21H,1,7-9,11-12H2,2-6H3/t16-,18+,20-,21-,23+,24+/m1/s1
SMILES:	C=C1[C@H]2C[C@@]3(C[C@@H]([C@@H]4C(C)(C)CCC[C@@]4(C)C3=CC2=O)OC(=O)C)[C@@H]1OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523412
PubChem CID:	25019754
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO33117	jungermannia atrobrunnea	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18665642]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	128.0	ug.mL-1	PMID[548948]

☑ 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 NPC176845 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	225
0.1-0.2	1285
0.2-0.3	4775
0.3-0.4	9606
0.4-0.5	11781
0.5-0.6	6278
0.6-0.7	5982
0.7-0.8	2536
0.8-0.85	205
0.85-0.9	23
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8854	High Similarity	NPC226986
0.8854	High Similarity	NPC23680
0.8791	High Similarity	NPC286153
0.8776	High Similarity	NPC474327
0.87	High Similarity	NPC189616
0.8687	High Similarity	NPC136289
0.866	High Similarity	NPC38530
0.866	High Similarity	NPC84335
0.8617	High Similarity	NPC152467
0.86	High Similarity	NPC36321
0.86	High Similarity	NPC254202
0.86	High Similarity	NPC236390
0.8587	High Similarity	NPC195640
0.8587	High Similarity	NPC220478
0.8586	High Similarity	NPC81530
0.8586	High Similarity	NPC310981
0.8571	High Similarity	NPC252295
0.8515	High Similarity	NPC119493
0.8511	High Similarity	NPC474679
0.85	High Similarity	NPC271266
0.85	High Similarity	NPC195290
0.85	High Similarity	NPC204450
0.85	High Similarity	NPC308351
0.8478	Intermediate Similarity	NPC323765
0.8476	Intermediate Similarity	NPC475524
0.8476	Intermediate Similarity	NPC100267
0.8469	Intermediate Similarity	NPC151488
0.8469	Intermediate Similarity	NPC292133
0.8454	Intermediate Similarity	NPC469599
0.8438	Intermediate Similarity	NPC79117
0.8416	Intermediate Similarity	NPC140723
0.8404	Intermediate Similarity	NPC28227
0.8404	Intermediate Similarity	NPC215831
0.8404	Intermediate Similarity	NPC477128
0.8387	Intermediate Similarity	NPC471042
0.8384	Intermediate Similarity	NPC153792
0.8384	Intermediate Similarity	NPC271387
0.8381	Intermediate Similarity	NPC470960
0.8367	Intermediate Similarity	NPC307164
0.8351	Intermediate Similarity	NPC477130
0.8351	Intermediate Similarity	NPC477129
0.835	Intermediate Similarity	NPC475294
0.835	Intermediate Similarity	NPC220974
0.8349	Intermediate Similarity	NPC475041
0.8333	Intermediate Similarity	NPC218301
0.8333	Intermediate Similarity	NPC235889
0.8333	Intermediate Similarity	NPC154101
0.8317	Intermediate Similarity	NPC22388
0.8317	Intermediate Similarity	NPC56498
0.8316	Intermediate Similarity	NPC73995
0.8316	Intermediate Similarity	NPC177141
0.8316	Intermediate Similarity	NPC284561
0.8316	Intermediate Similarity	NPC473647
0.8302	Intermediate Similarity	NPC71348
0.83	Intermediate Similarity	NPC218383
0.83	Intermediate Similarity	NPC205899
0.83	Intermediate Similarity	NPC470906
0.83	Intermediate Similarity	NPC476274
0.8286	Intermediate Similarity	NPC197428
0.8283	Intermediate Similarity	NPC69385
0.8283	Intermediate Similarity	NPC18319
0.8283	Intermediate Similarity	NPC110937
0.8269	Intermediate Similarity	NPC189075
0.8269	Intermediate Similarity	NPC470269
0.8269	Intermediate Similarity	NPC275539
0.8265	Intermediate Similarity	NPC470974
0.8265	Intermediate Similarity	NPC470978
0.8265	Intermediate Similarity	NPC470016
0.8265	Intermediate Similarity	NPC274417
0.8265	Intermediate Similarity	NPC317586
0.8265	Intermediate Similarity	NPC33473
0.8261	Intermediate Similarity	NPC170862
0.8257	Intermediate Similarity	NPC311554
0.8257	Intermediate Similarity	NPC257457
0.8252	Intermediate Similarity	NPC278628
0.8252	Intermediate Similarity	NPC181265
0.8252	Intermediate Similarity	NPC231530
0.8252	Intermediate Similarity	NPC60681
0.8252	Intermediate Similarity	NPC475571
0.8252	Intermediate Similarity	NPC470267
0.8247	Intermediate Similarity	NPC470375
0.8247	Intermediate Similarity	NPC470376
0.8241	Intermediate Similarity	NPC190286
0.8241	Intermediate Similarity	NPC148458
0.8235	Intermediate Similarity	NPC471364
0.8235	Intermediate Similarity	NPC132395
0.8235	Intermediate Similarity	NPC471365
0.8229	Intermediate Similarity	NPC220454
0.8229	Intermediate Similarity	NPC212679
0.8229	Intermediate Similarity	NPC469595
0.8229	Intermediate Similarity	NPC8062
0.8224	Intermediate Similarity	NPC962
0.8224	Intermediate Similarity	NPC250109
0.8218	Intermediate Similarity	NPC476223
0.8218	Intermediate Similarity	NPC224720
0.8218	Intermediate Similarity	NPC476240
0.82	Intermediate Similarity	NPC197386
0.82	Intermediate Similarity	NPC10364
0.82	Intermediate Similarity	NPC222011
0.819	Intermediate Similarity	NPC258543
0.819	Intermediate Similarity	NPC112457
0.819	Intermediate Similarity	NPC241927
0.8182	Intermediate Similarity	NPC328371
0.8182	Intermediate Similarity	NPC322063
0.8182	Intermediate Similarity	NPC111684
0.8182	Intermediate Similarity	NPC95565
0.8182	Intermediate Similarity	NPC58052
0.8173	Intermediate Similarity	NPC44063
0.8173	Intermediate Similarity	NPC110496
0.8173	Intermediate Similarity	NPC471601
0.8165	Intermediate Similarity	NPC239273
0.8163	Intermediate Similarity	NPC470697
0.8163	Intermediate Similarity	NPC84893
0.8163	Intermediate Similarity	NPC269729
0.8163	Intermediate Similarity	NPC294266
0.8163	Intermediate Similarity	NPC166906
0.8163	Intermediate Similarity	NPC476415
0.8155	Intermediate Similarity	NPC164835
0.8155	Intermediate Similarity	NPC96268
0.8155	Intermediate Similarity	NPC228669
0.8155	Intermediate Similarity	NPC28656
0.8144	Intermediate Similarity	NPC221282
0.8144	Intermediate Similarity	NPC49420
0.8137	Intermediate Similarity	NPC308726
0.8137	Intermediate Similarity	NPC185530
0.8137	Intermediate Similarity	NPC119601
0.8137	Intermediate Similarity	NPC170615
0.8131	Intermediate Similarity	NPC221144
0.8131	Intermediate Similarity	NPC476163
0.8131	Intermediate Similarity	NPC264634
0.8125	Intermediate Similarity	NPC269642
0.8125	Intermediate Similarity	NPC477943
0.8125	Intermediate Similarity	NPC305039
0.8119	Intermediate Similarity	NPC117685
0.8119	Intermediate Similarity	NPC476303
0.8119	Intermediate Similarity	NPC476933
0.8113	Intermediate Similarity	NPC253906
0.81	Intermediate Similarity	NPC175351
0.81	Intermediate Similarity	NPC475894
0.81	Intermediate Similarity	NPC121402
0.81	Intermediate Similarity	NPC132753
0.81	Intermediate Similarity	NPC253826
0.81	Intermediate Similarity	NPC107243
0.81	Intermediate Similarity	NPC151681
0.81	Intermediate Similarity	NPC224356
0.81	Intermediate Similarity	NPC57416
0.81	Intermediate Similarity	NPC474343
0.8095	Intermediate Similarity	NPC94529
0.8095	Intermediate Similarity	NPC177064
0.8091	Intermediate Similarity	NPC470420
0.8091	Intermediate Similarity	NPC153440
0.8085	Intermediate Similarity	NPC470223
0.8085	Intermediate Similarity	NPC110405
0.8085	Intermediate Similarity	NPC189311
0.8081	Intermediate Similarity	NPC173875
0.8081	Intermediate Similarity	NPC280877
0.8081	Intermediate Similarity	NPC184848
0.8081	Intermediate Similarity	NPC69548
0.8081	Intermediate Similarity	NPC174948
0.8081	Intermediate Similarity	NPC469995
0.8081	Intermediate Similarity	NPC318282
0.8077	Intermediate Similarity	NPC469607
0.8073	Intermediate Similarity	NPC270958
0.8073	Intermediate Similarity	NPC266728
0.8073	Intermediate Similarity	NPC49492
0.8065	Intermediate Similarity	NPC193198
0.8065	Intermediate Similarity	NPC470047
0.8065	Intermediate Similarity	NPC470046
0.8061	Intermediate Similarity	NPC475700
0.8061	Intermediate Similarity	NPC109414
0.8061	Intermediate Similarity	NPC474185
0.8061	Intermediate Similarity	NPC25750
0.8058	Intermediate Similarity	NPC176883
0.8058	Intermediate Similarity	NPC26478
0.8058	Intermediate Similarity	NPC55872
0.8058	Intermediate Similarity	NPC159442
0.8058	Intermediate Similarity	NPC470954
0.8056	Intermediate Similarity	NPC202889
0.8056	Intermediate Similarity	NPC52634
0.8043	Intermediate Similarity	NPC475665
0.8041	Intermediate Similarity	NPC273199
0.8041	Intermediate Similarity	NPC475965
0.8041	Intermediate Similarity	NPC471896
0.8041	Intermediate Similarity	NPC161638
0.8041	Intermediate Similarity	NPC474842
0.8041	Intermediate Similarity	NPC328141
0.8039	Intermediate Similarity	NPC163372
0.8039	Intermediate Similarity	NPC99411
0.8039	Intermediate Similarity	NPC168319
0.8039	Intermediate Similarity	NPC194028
0.8039	Intermediate Similarity	NPC302537
0.8037	Intermediate Similarity	NPC43775
0.8037	Intermediate Similarity	NPC214797
0.8037	Intermediate Similarity	NPC118860
0.8037	Intermediate Similarity	NPC231589
0.8021	Intermediate Similarity	NPC474845
0.8021	Intermediate Similarity	NPC226863
0.802	Intermediate Similarity	NPC114274
0.802	Intermediate Similarity	NPC478056
0.802	Intermediate Similarity	NPC477813

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 NPC176845 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1500
0.2-0.3	3894
0.3-0.4	2324
0.4-0.5	757
0.5-0.6	185
0.6-0.7	139
0.7-0.8	118
0.8-0.85	41
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8614	High Similarity	NPD6008	Approved
0.8587	High Similarity	NPD7334	Approved
0.8587	High Similarity	NPD6409	Approved
0.8587	High Similarity	NPD7146	Approved
0.8587	High Similarity	NPD6684	Approved
0.8587	High Similarity	NPD7521	Approved
0.8587	High Similarity	NPD5330	Approved
0.8454	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD6402	Approved
0.8431	Intermediate Similarity	NPD5739	Approved
0.8431	Intermediate Similarity	NPD7128	Approved
0.8431	Intermediate Similarity	NPD6675	Approved
0.8404	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8404	Intermediate Similarity	NPD6903	Approved
0.8365	Intermediate Similarity	NPD6373	Approved
0.8365	Intermediate Similarity	NPD6372	Approved
0.8333	Intermediate Similarity	NPD5693	Phase 1
0.8269	Intermediate Similarity	NPD6899	Approved
0.8269	Intermediate Similarity	NPD6881	Approved
0.8269	Intermediate Similarity	NPD7320	Approved
0.8247	Intermediate Similarity	NPD6399	Phase 3
0.8211	Intermediate Similarity	NPD6672	Approved
0.8211	Intermediate Similarity	NPD5737	Approved
0.8208	Intermediate Similarity	NPD6650	Approved
0.8208	Intermediate Similarity	NPD6649	Approved
0.8173	Intermediate Similarity	NPD5697	Approved
0.8173	Intermediate Similarity	NPD5701	Approved
0.8163	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD7900	Approved
0.8125	Intermediate Similarity	NPD6673	Approved
0.8125	Intermediate Similarity	NPD6904	Approved
0.8125	Intermediate Similarity	NPD6080	Approved
0.8113	Intermediate Similarity	NPD7102	Approved
0.8113	Intermediate Similarity	NPD6883	Approved
0.8113	Intermediate Similarity	NPD7290	Approved
0.8095	Intermediate Similarity	NPD6011	Approved
0.8037	Intermediate Similarity	NPD6869	Approved
0.8037	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD8130	Phase 1
0.8037	Intermediate Similarity	NPD6847	Approved
0.8037	Intermediate Similarity	NPD6617	Approved
0.8019	Intermediate Similarity	NPD6013	Approved
0.8019	Intermediate Similarity	NPD6014	Approved
0.8019	Intermediate Similarity	NPD6012	Approved
0.798	Intermediate Similarity	NPD6001	Approved
0.7963	Intermediate Similarity	NPD6882	Approved
0.7963	Intermediate Similarity	NPD8297	Approved
0.7938	Intermediate Similarity	NPD5328	Approved
0.7921	Intermediate Similarity	NPD6084	Phase 2
0.7921	Intermediate Similarity	NPD6083	Phase 2
0.7921	Intermediate Similarity	NPD7902	Approved
0.7921	Intermediate Similarity	NPD4755	Approved
0.7895	Intermediate Similarity	NPD1694	Approved
0.7843	Intermediate Similarity	NPD5696	Approved
0.7843	Intermediate Similarity	NPD7638	Approved
0.7835	Intermediate Similarity	NPD5208	Approved
0.7812	Intermediate Similarity	NPD6098	Approved
0.78	Intermediate Similarity	NPD7748	Approved
0.7788	Intermediate Similarity	NPD5211	Phase 2
0.7778	Intermediate Similarity	NPD6050	Approved
0.7778	Intermediate Similarity	NPD6079	Approved
0.7767	Intermediate Similarity	NPD5286	Approved
0.7767	Intermediate Similarity	NPD4700	Approved
0.7767	Intermediate Similarity	NPD4696	Approved
0.7767	Intermediate Similarity	NPD5285	Approved
0.7767	Intermediate Similarity	NPD7640	Approved
0.7767	Intermediate Similarity	NPD7639	Approved
0.7766	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6051	Approved
0.7732	Intermediate Similarity	NPD3573	Approved
0.7723	Intermediate Similarity	NPD5695	Phase 3
0.77	Intermediate Similarity	NPD4202	Approved
0.7692	Intermediate Similarity	NPD5223	Approved
0.7679	Intermediate Similarity	NPD7115	Discovery
0.7677	Intermediate Similarity	NPD5207	Approved
0.7677	Intermediate Similarity	NPD5692	Phase 3
0.7647	Intermediate Similarity	NPD4697	Phase 3
0.7642	Intermediate Similarity	NPD5141	Approved
0.7629	Intermediate Similarity	NPD3618	Phase 1
0.7619	Intermediate Similarity	NPD4633	Approved
0.7619	Intermediate Similarity	NPD5226	Approved
0.7619	Intermediate Similarity	NPD5224	Approved
0.7619	Intermediate Similarity	NPD5225	Approved
0.7611	Intermediate Similarity	NPD6335	Approved
0.7604	Intermediate Similarity	NPD3665	Phase 1
0.7604	Intermediate Similarity	NPD3666	Approved
0.7604	Intermediate Similarity	NPD3133	Approved
0.76	Intermediate Similarity	NPD7515	Phase 2
0.76	Intermediate Similarity	NPD5281	Approved
0.76	Intermediate Similarity	NPD5694	Approved
0.76	Intermediate Similarity	NPD5284	Approved
0.7589	Intermediate Similarity	NPD6274	Approved
0.7568	Intermediate Similarity	NPD4632	Approved
0.7547	Intermediate Similarity	NPD4754	Approved
0.7547	Intermediate Similarity	NPD5174	Approved
0.7547	Intermediate Similarity	NPD5175	Approved
0.7544	Intermediate Similarity	NPD7100	Approved
0.7544	Intermediate Similarity	NPD7101	Approved
0.7522	Intermediate Similarity	NPD6317	Approved
0.7477	Intermediate Similarity	NPD6053	Discontinued
0.7476	Intermediate Similarity	NPD5221	Approved
0.7476	Intermediate Similarity	NPD5222	Approved
0.7476	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6313	Approved
0.7456	Intermediate Similarity	NPD6314	Approved
0.7426	Intermediate Similarity	NPD8035	Phase 2
0.7426	Intermediate Similarity	NPD8034	Phase 2
0.7423	Intermediate Similarity	NPD4786	Approved
0.7414	Intermediate Similarity	NPD6909	Approved
0.7414	Intermediate Similarity	NPD6908	Approved
0.7414	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4767	Approved
0.7407	Intermediate Similarity	NPD4768	Approved
0.7404	Intermediate Similarity	NPD5173	Approved
0.74	Intermediate Similarity	NPD4753	Phase 2
0.7396	Intermediate Similarity	NPD4221	Approved
0.7396	Intermediate Similarity	NPD4223	Phase 3
0.7383	Intermediate Similarity	NPD6052	Approved
0.7368	Intermediate Similarity	NPD6009	Approved
0.7347	Intermediate Similarity	NPD5329	Approved
0.7328	Intermediate Similarity	NPD6319	Approved
0.7311	Intermediate Similarity	NPD7507	Approved
0.7288	Intermediate Similarity	NPD7604	Phase 2
0.7281	Intermediate Similarity	NPD6868	Approved
0.7273	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4729	Approved
0.7273	Intermediate Similarity	NPD5128	Approved
0.7273	Intermediate Similarity	NPD4730	Approved
0.7265	Intermediate Similarity	NPD5983	Phase 2
0.7245	Intermediate Similarity	NPD3668	Phase 3
0.7245	Intermediate Similarity	NPD4197	Approved
0.7227	Intermediate Similarity	NPD7492	Approved
0.7216	Intermediate Similarity	NPD3667	Approved
0.7212	Intermediate Similarity	NPD4629	Approved
0.7212	Intermediate Similarity	NPD5210	Approved
0.7212	Intermediate Similarity	NPD5654	Approved
0.7182	Intermediate Similarity	NPD6614	Approved
0.7182	Intermediate Similarity	NPD6412	Phase 2
0.7182	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6059	Approved
0.7179	Intermediate Similarity	NPD6054	Approved
0.717	Intermediate Similarity	NPD4225	Approved
0.7167	Intermediate Similarity	NPD6336	Discontinued
0.7167	Intermediate Similarity	NPD6616	Approved
0.7157	Intermediate Similarity	NPD5785	Approved
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5135	Approved
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD5250	Approved
0.7131	Intermediate Similarity	NPD7319	Approved
0.713	Intermediate Similarity	NPD7632	Discontinued
0.7107	Intermediate Similarity	NPD8293	Discontinued
0.7107	Intermediate Similarity	NPD7078	Approved
0.71	Intermediate Similarity	NPD4688	Approved
0.71	Intermediate Similarity	NPD4693	Phase 3
0.71	Intermediate Similarity	NPD4690	Approved
0.71	Intermediate Similarity	NPD5205	Approved
0.71	Intermediate Similarity	NPD4689	Approved
0.71	Intermediate Similarity	NPD4138	Approved
0.7087	Intermediate Similarity	NPD6411	Approved
0.708	Intermediate Similarity	NPD5127	Approved
0.708	Intermediate Similarity	NPD5215	Approved
0.708	Intermediate Similarity	NPD5216	Approved
0.708	Intermediate Similarity	NPD5217	Approved
0.7075	Intermediate Similarity	NPD5959	Approved
0.7059	Intermediate Similarity	NPD6370	Approved
0.7049	Intermediate Similarity	NPD7736	Approved
0.7048	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6016	Approved
0.6975	Remote Similarity	NPD6015	Approved
0.6964	Remote Similarity	NPD6686	Approved
0.6957	Remote Similarity	NPD4747	Approved
0.6931	Remote Similarity	NPD5279	Phase 3
0.6931	Remote Similarity	NPD4694	Approved
0.6931	Remote Similarity	NPD5280	Approved
0.6931	Remote Similarity	NPD5690	Phase 2
0.6917	Remote Similarity	NPD5988	Approved
0.6903	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5167	Approved
0.6893	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6101	Approved
0.6882	Remote Similarity	NPD5777	Approved
0.6869	Remote Similarity	NPD6435	Approved
0.6848	Remote Similarity	NPD4137	Phase 3
0.6837	Remote Similarity	NPD4695	Discontinued
0.6822	Remote Similarity	NPD7732	Phase 3
0.6814	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5168	Approved
0.681	Remote Similarity	NPD6858	Approved
0.681	Remote Similarity	NPD7094	Approved
0.68	Remote Similarity	NPD4788	Approved
0.6774	Remote Similarity	NPD6033	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