NPASS Compound

Structure

NPC24816 OpenBabel07101719132D 25 27 0 0 1 0 0 0 0 0999 V2000 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 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 -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 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 -4.3301 3.5000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 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 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 6 25 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 6 0 0 0 18 25 1 1 0 0 0 19 21 1 6 0 0 0 19 22 1 0 0 0 0 20 22 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 4 1 6 0 0 0 22 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.25
Volume:	381.86
LogP:	4.433
LogD:	3.846
LogS:	-4.225
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.759
Synthetic Accessibility Score:	4.525
Fsp3:	0.773
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:	-5.033
MDCK Permeability:	3.806905806413852e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.817
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	98.42522430419922%
Volume Distribution (VD):	0.618
Pgp-substrate:	2.5618298053741455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.554
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.338
CYP2C9-substrate:	0.132
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.244
CYP3A4-substrate:	0.385

ADMET: Excretion

Clearance (CL):	1.029
Half-life (T1/2):	0.433

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.537
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.931
Carcinogencity:	0.246
Eye Corrosion:	0.486
Eye Irritation:	0.955
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC24816

Natural Product ID:	NPC24816
*Common Name:**	Aquilarabietic Acid J
IUPAC Name:	(1R,4aR,4bR,6S,10aR)-6-ethoxy-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid
Synonyms:	Aquilarabietic acid J
Standard InCHIKey:	SEYOTWWUZJJIRX-JIWOIOHBSA-N
Standard InCHI:	InChI=1S/C22H34O3/c1-6-25-18-13-17-15(12-16(18)14(2)3)8-9-19-21(17,4)10-7-11-22(19,5)20(23)24/h8,12,14,17-19H,6-7,9-11,13H2,1-5H3,(H,23,24)/t17-,18-,19+,21+,22+/m0/s1
SMILES:	CCO[C@H]1C[C@H]2C(=CC[C@@H]3[C@]2(C)CCC[C@@]3(C)C(=O)O)C=C1C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333387
PubChem CID:	71578635
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
NPO33033	chinese eaglewood	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23394318]

☑ 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
Others	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1072	Individual Protein	Serotonin transporter	Rattus norvegicus	Inhibition	=	51.1	%	PMID[463772]
NPT2	Others	Unspecified		Inhibition	=	13.4	%	PMID[463772]

☑ 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 NPC24816 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	173
0.1-0.2	906
0.2-0.3	3737
0.3-0.4	10040
0.4-0.5	13198
0.5-0.6	7428
0.6-0.7	5249
0.7-0.8	1851
0.8-0.85	104
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.878	High Similarity	NPC4827
0.869	High Similarity	NPC14203
0.869	High Similarity	NPC229584
0.8667	High Similarity	NPC169343
0.8652	High Similarity	NPC198818
0.8621	High Similarity	NPC322159
0.8621	High Similarity	NPC325594
0.8571	High Similarity	NPC91010
0.8571	High Similarity	NPC469406
0.8539	High Similarity	NPC84271
0.8539	High Similarity	NPC77168
0.8539	High Similarity	NPC102414
0.8537	High Similarity	NPC899
0.8537	High Similarity	NPC309399
0.8523	High Similarity	NPC171722
0.8506	High Similarity	NPC470048
0.8471	Intermediate Similarity	NPC327002
0.8452	Intermediate Similarity	NPC242767
0.8452	Intermediate Similarity	NPC327674
0.8444	Intermediate Similarity	NPC472307
0.8444	Intermediate Similarity	NPC111585
0.8444	Intermediate Similarity	NPC469595
0.8444	Intermediate Similarity	NPC175628
0.8444	Intermediate Similarity	NPC148414
0.8444	Intermediate Similarity	NPC212679
0.8444	Intermediate Similarity	NPC220454
0.8409	Intermediate Similarity	NPC73038
0.8409	Intermediate Similarity	NPC82979
0.8372	Intermediate Similarity	NPC15910
0.837	Intermediate Similarity	NPC471720
0.8352	Intermediate Similarity	NPC477574
0.8352	Intermediate Similarity	NPC301244
0.8352	Intermediate Similarity	NPC26888
0.8333	Intermediate Similarity	NPC284561
0.8333	Intermediate Similarity	NPC161751
0.8333	Intermediate Similarity	NPC474972
0.8333	Intermediate Similarity	NPC95246
0.8333	Intermediate Similarity	NPC5509
0.8333	Intermediate Similarity	NPC321514
0.8333	Intermediate Similarity	NPC474889
0.8315	Intermediate Similarity	NPC187376
0.8315	Intermediate Similarity	NPC159046
0.8315	Intermediate Similarity	NPC233836
0.8315	Intermediate Similarity	NPC312561
0.8315	Intermediate Similarity	NPC71507
0.8315	Intermediate Similarity	NPC231599
0.8295	Intermediate Similarity	NPC52628
0.8295	Intermediate Similarity	NPC76333
0.8293	Intermediate Similarity	NPC306928
0.8293	Intermediate Similarity	NPC301065
0.828	Intermediate Similarity	NPC295347
0.828	Intermediate Similarity	NPC171395
0.8276	Intermediate Similarity	NPC83569
0.8276	Intermediate Similarity	NPC69279
0.8261	Intermediate Similarity	NPC271652
0.8261	Intermediate Similarity	NPC115021
0.8256	Intermediate Similarity	NPC474955
0.8256	Intermediate Similarity	NPC40228
0.8256	Intermediate Similarity	NPC473420
0.8256	Intermediate Similarity	NPC142244
0.8242	Intermediate Similarity	NPC469372
0.8242	Intermediate Similarity	NPC120840
0.8242	Intermediate Similarity	NPC113989
0.8242	Intermediate Similarity	NPC221111
0.8242	Intermediate Similarity	NPC474728
0.8242	Intermediate Similarity	NPC280149
0.8242	Intermediate Similarity	NPC471896
0.8229	Intermediate Similarity	NPC476888
0.8229	Intermediate Similarity	NPC93744
0.8229	Intermediate Similarity	NPC99411
0.8222	Intermediate Similarity	NPC477128
0.8222	Intermediate Similarity	NPC40552
0.8222	Intermediate Similarity	NPC246708
0.8222	Intermediate Similarity	NPC472302
0.8211	Intermediate Similarity	NPC48647
0.8211	Intermediate Similarity	NPC478056
0.8211	Intermediate Similarity	NPC108368
0.8211	Intermediate Similarity	NPC57079
0.8211	Intermediate Similarity	NPC124703
0.8211	Intermediate Similarity	NPC477813
0.8211	Intermediate Similarity	NPC471717
0.8211	Intermediate Similarity	NPC234617
0.8211	Intermediate Similarity	NPC92275
0.8202	Intermediate Similarity	NPC473226
0.8202	Intermediate Similarity	NPC28252
0.8202	Intermediate Similarity	NPC55309
0.8202	Intermediate Similarity	NPC220478
0.8191	Intermediate Similarity	NPC78473
0.8191	Intermediate Similarity	NPC190713
0.8182	Intermediate Similarity	NPC165064
0.8172	Intermediate Similarity	NPC38830
0.8172	Intermediate Similarity	NPC477129
0.8172	Intermediate Similarity	NPC80365
0.8172	Intermediate Similarity	NPC476415
0.8172	Intermediate Similarity	NPC477130
0.8163	Intermediate Similarity	NPC473175
0.8161	Intermediate Similarity	NPC73882
0.8152	Intermediate Similarity	NPC77099
0.8152	Intermediate Similarity	NPC186363
0.8152	Intermediate Similarity	NPC297265
0.8152	Intermediate Similarity	NPC233345
0.8152	Intermediate Similarity	NPC49420
0.8152	Intermediate Similarity	NPC60755
0.8152	Intermediate Similarity	NPC470590
0.8152	Intermediate Similarity	NPC303697
0.8152	Intermediate Similarity	NPC285184
0.8144	Intermediate Similarity	NPC114540
0.8144	Intermediate Similarity	NPC273005
0.8144	Intermediate Similarity	NPC476890
0.8144	Intermediate Similarity	NPC31058
0.8144	Intermediate Similarity	NPC32577
0.8144	Intermediate Similarity	NPC469606
0.8144	Intermediate Similarity	NPC155332
0.8144	Intermediate Similarity	NPC40918
0.814	Intermediate Similarity	NPC104545
0.814	Intermediate Similarity	NPC195424
0.8132	Intermediate Similarity	NPC474686
0.8132	Intermediate Similarity	NPC174342
0.8132	Intermediate Similarity	NPC470588
0.8132	Intermediate Similarity	NPC475049
0.8132	Intermediate Similarity	NPC30522
0.8132	Intermediate Similarity	NPC173042
0.8132	Intermediate Similarity	NPC281524
0.8125	Intermediate Similarity	NPC201406
0.8125	Intermediate Similarity	NPC474012
0.8125	Intermediate Similarity	NPC476299
0.8118	Intermediate Similarity	NPC179028
0.8118	Intermediate Similarity	NPC239098
0.8111	Intermediate Similarity	NPC307426
0.8111	Intermediate Similarity	NPC167877
0.8111	Intermediate Similarity	NPC51700
0.8111	Intermediate Similarity	NPC102683
0.8111	Intermediate Similarity	NPC474684
0.8111	Intermediate Similarity	NPC18064
0.8111	Intermediate Similarity	NPC477228
0.8111	Intermediate Similarity	NPC98442
0.8111	Intermediate Similarity	NPC68160
0.8111	Intermediate Similarity	NPC293564
0.8111	Intermediate Similarity	NPC142361
0.8111	Intermediate Similarity	NPC242468
0.8111	Intermediate Similarity	NPC142415
0.8111	Intermediate Similarity	NPC171203
0.8111	Intermediate Similarity	NPC130577
0.8111	Intermediate Similarity	NPC88716
0.8105	Intermediate Similarity	NPC285513
0.8105	Intermediate Similarity	NPC208094
0.8105	Intermediate Similarity	NPC253826
0.8105	Intermediate Similarity	NPC202705
0.8105	Intermediate Similarity	NPC254496
0.809	Intermediate Similarity	NPC189311
0.809	Intermediate Similarity	NPC86316
0.809	Intermediate Similarity	NPC474083
0.809	Intermediate Similarity	NPC106416
0.809	Intermediate Similarity	NPC65661
0.8085	Intermediate Similarity	NPC183012
0.8085	Intermediate Similarity	NPC222845
0.8085	Intermediate Similarity	NPC20546
0.8085	Intermediate Similarity	NPC162001
0.8085	Intermediate Similarity	NPC45324
0.8081	Intermediate Similarity	NPC469607
0.8081	Intermediate Similarity	NPC266570
0.8068	Intermediate Similarity	NPC52108
0.8068	Intermediate Similarity	NPC193198
0.8068	Intermediate Similarity	NPC470948
0.8068	Intermediate Similarity	NPC474789
0.8068	Intermediate Similarity	NPC470047
0.8068	Intermediate Similarity	NPC470046
0.8068	Intermediate Similarity	NPC70834
0.8065	Intermediate Similarity	NPC49776
0.8065	Intermediate Similarity	NPC139692
0.8065	Intermediate Similarity	NPC474436
0.8065	Intermediate Similarity	NPC66429
0.8065	Intermediate Similarity	NPC63118
0.8065	Intermediate Similarity	NPC470224
0.8065	Intermediate Similarity	NPC152897
0.8065	Intermediate Similarity	NPC86368
0.8061	Intermediate Similarity	NPC476889
0.8061	Intermediate Similarity	NPC36688
0.8049	Intermediate Similarity	NPC160817
0.8046	Intermediate Similarity	NPC201912
0.8046	Intermediate Similarity	NPC38350
0.8043	Intermediate Similarity	NPC476437
0.8043	Intermediate Similarity	NPC8062
0.8043	Intermediate Similarity	NPC232426
0.8043	Intermediate Similarity	NPC469400
0.8043	Intermediate Similarity	NPC476369
0.8043	Intermediate Similarity	NPC477149
0.8043	Intermediate Similarity	NPC477147
0.8043	Intermediate Similarity	NPC113393
0.8043	Intermediate Similarity	NPC69622
0.8043	Intermediate Similarity	NPC281942
0.8041	Intermediate Similarity	NPC469657
0.8041	Intermediate Similarity	NPC235142
0.8041	Intermediate Similarity	NPC244456
0.8041	Intermediate Similarity	NPC472637
0.8023	Intermediate Similarity	NPC231431
0.8022	Intermediate Similarity	NPC97884
0.8022	Intermediate Similarity	NPC290690
0.8022	Intermediate Similarity	NPC182797
0.8022	Intermediate Similarity	NPC472220

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 NPC24816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1179
0.2-0.3	3405
0.3-0.4	2713
0.4-0.5	1097
0.5-0.6	356
0.6-0.7	196
0.7-0.8	43
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
0.7979	Intermediate Similarity	NPD7748	Approved
0.7976	Intermediate Similarity	NPD8039	Approved
0.7957	Intermediate Similarity	NPD6411	Approved
0.7872	Intermediate Similarity	NPD6399	Phase 3
0.7835	Intermediate Similarity	NPD7638	Approved
0.7802	Intermediate Similarity	NPD5330	Approved
0.7802	Intermediate Similarity	NPD7521	Approved
0.7802	Intermediate Similarity	NPD7334	Approved
0.7802	Intermediate Similarity	NPD7146	Approved
0.7802	Intermediate Similarity	NPD6684	Approved
0.7802	Intermediate Similarity	NPD6409	Approved
0.7766	Intermediate Similarity	NPD7515	Phase 2
0.7755	Intermediate Similarity	NPD7640	Approved
0.7755	Intermediate Similarity	NPD7639	Approved
0.7753	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6101	Approved
0.7732	Intermediate Similarity	NPD7902	Approved
0.7692	Intermediate Similarity	NPD1694	Approved
0.7684	Intermediate Similarity	NPD5778	Approved
0.7684	Intermediate Similarity	NPD5779	Approved
0.7634	Intermediate Similarity	NPD6903	Approved
0.7634	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5279	Phase 3
0.7582	Intermediate Similarity	NPD4786	Approved
0.7556	Intermediate Similarity	NPD3667	Approved
0.7553	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5695	Phase 3
0.7447	Intermediate Similarity	NPD5737	Approved
0.7447	Intermediate Similarity	NPD6672	Approved
0.7423	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7900	Approved
0.7419	Intermediate Similarity	NPD3618	Phase 1
0.7396	Intermediate Similarity	NPD5281	Approved
0.7396	Intermediate Similarity	NPD5284	Approved
0.7396	Intermediate Similarity	NPD6050	Approved
0.7391	Intermediate Similarity	NPD3133	Approved
0.7391	Intermediate Similarity	NPD3666	Approved
0.7391	Intermediate Similarity	NPD3665	Phase 1
0.7374	Intermediate Similarity	NPD6084	Phase 2
0.7374	Intermediate Similarity	NPD6083	Phase 2
0.7368	Intermediate Similarity	NPD5328	Approved
0.7368	Intermediate Similarity	NPD6051	Approved
0.7312	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5207	Approved
0.7292	Intermediate Similarity	NPD5692	Phase 3
0.7238	Intermediate Similarity	NPD6686	Approved
0.7234	Intermediate Similarity	NPD4694	Approved
0.7234	Intermediate Similarity	NPD6098	Approved
0.7234	Intermediate Similarity	NPD5280	Approved
0.7228	Intermediate Similarity	NPD6404	Discontinued
0.7216	Intermediate Similarity	NPD5694	Approved
0.7216	Intermediate Similarity	NPD8034	Phase 2
0.7216	Intermediate Similarity	NPD6079	Approved
0.7216	Intermediate Similarity	NPD5693	Phase 1
0.7216	Intermediate Similarity	NPD8035	Phase 2
0.7212	Intermediate Similarity	NPD7128	Approved
0.7212	Intermediate Similarity	NPD5739	Approved
0.7212	Intermediate Similarity	NPD6675	Approved
0.7212	Intermediate Similarity	NPD6402	Approved
0.7182	Intermediate Similarity	NPD7115	Discovery
0.7158	Intermediate Similarity	NPD3573	Approved
0.7129	Intermediate Similarity	NPD4225	Approved
0.7129	Intermediate Similarity	NPD5696	Approved
0.7087	Intermediate Similarity	NPD7632	Discontinued
0.7075	Intermediate Similarity	NPD7320	Approved
0.7075	Intermediate Similarity	NPD6881	Approved
0.7075	Intermediate Similarity	NPD6899	Approved
0.7053	Intermediate Similarity	NPD4623	Approved
0.7053	Intermediate Similarity	NPD4519	Discontinued
0.7041	Intermediate Similarity	NPD7637	Suspended
0.7033	Intermediate Similarity	NPD7645	Phase 2
0.7021	Intermediate Similarity	NPD3668	Phase 3
0.701	Intermediate Similarity	NPD6673	Approved
0.701	Intermediate Similarity	NPD6904	Approved
0.701	Intermediate Similarity	NPD6080	Approved
0.7009	Intermediate Similarity	NPD6372	Approved
0.7009	Intermediate Similarity	NPD6373	Approved
0.7009	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4223	Phase 3
0.6989	Remote Similarity	NPD4221	Approved
0.6988	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5697	Approved
0.6981	Remote Similarity	NPD5701	Approved
0.697	Remote Similarity	NPD4202	Approved
0.6966	Remote Similarity	NPD8264	Approved
0.6957	Remote Similarity	NPD4695	Discontinued
0.6947	Remote Similarity	NPD5329	Approved
0.6944	Remote Similarity	NPD7290	Approved
0.6944	Remote Similarity	NPD7102	Approved
0.6944	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6011	Approved
0.6907	Remote Similarity	NPD5208	Approved
0.6881	Remote Similarity	NPD6869	Approved
0.6881	Remote Similarity	NPD6649	Approved
0.6881	Remote Similarity	NPD6650	Approved
0.6881	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8130	Phase 1
0.6881	Remote Similarity	NPD6847	Approved
0.6881	Remote Similarity	NPD6617	Approved
0.6875	Remote Similarity	NPD5690	Phase 2
0.6854	Remote Similarity	NPD5733	Approved
0.6852	Remote Similarity	NPD6013	Approved
0.6852	Remote Similarity	NPD6014	Approved
0.6852	Remote Similarity	NPD6012	Approved
0.6842	Remote Similarity	NPD4197	Approved
0.6837	Remote Similarity	NPD4753	Phase 2
0.6832	Remote Similarity	NPD5654	Approved
0.6818	Remote Similarity	NPD6053	Discontinued
0.6818	Remote Similarity	NPD8297	Approved
0.6818	Remote Similarity	NPD6882	Approved
0.6778	Remote Similarity	NPD6942	Approved
0.6778	Remote Similarity	NPD7339	Approved
0.6768	Remote Similarity	NPD4096	Approved
0.6768	Remote Similarity	NPD46	Approved
0.6768	Remote Similarity	NPD6698	Approved
0.6768	Remote Similarity	NPD5785	Approved
0.6765	Remote Similarity	NPD4697	Phase 3
0.6765	Remote Similarity	NPD5221	Approved
0.6765	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7614	Phase 1
0.6765	Remote Similarity	NPD5222	Approved
0.6739	Remote Similarity	NPD3617	Approved
0.6737	Remote Similarity	NPD5362	Discontinued
0.6737	Remote Similarity	NPD7154	Phase 3
0.6733	Remote Similarity	NPD6001	Approved
0.6703	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4139	Approved
0.6702	Remote Similarity	NPD4692	Approved
0.6701	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4693	Phase 3
0.6701	Remote Similarity	NPD4138	Approved
0.6701	Remote Similarity	NPD4688	Approved
0.6701	Remote Similarity	NPD4690	Approved
0.6701	Remote Similarity	NPD4689	Approved
0.6701	Remote Similarity	NPD5205	Approved
0.6699	Remote Similarity	NPD5959	Approved
0.6699	Remote Similarity	NPD4755	Approved
0.6699	Remote Similarity	NPD5173	Approved
0.6697	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6412	Phase 2
0.6637	Remote Similarity	NPD6868	Approved
0.6634	Remote Similarity	NPD5133	Approved
0.6632	Remote Similarity	NPD5209	Approved
0.6629	Remote Similarity	NPD5276	Approved
0.6606	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5211	Phase 2
0.6602	Remote Similarity	NPD7732	Phase 3
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7525	Registered
0.6596	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6008	Approved
0.6571	Remote Similarity	NPD5286	Approved
0.6571	Remote Similarity	NPD4700	Approved
0.6571	Remote Similarity	NPD5285	Approved
0.6571	Remote Similarity	NPD4696	Approved
0.6566	Remote Similarity	NPD4518	Approved
0.6562	Remote Similarity	NPD4788	Approved
0.6562	Remote Similarity	NPD6695	Phase 3
0.6555	Remote Similarity	NPD7507	Approved
0.6549	Remote Similarity	NPD6010	Discontinued
0.6535	Remote Similarity	NPD7983	Approved
0.6531	Remote Similarity	NPD6422	Discontinued
0.6522	Remote Similarity	NPD6933	Approved
0.6522	Remote Similarity	NPD6117	Approved
0.6522	Remote Similarity	NPD6335	Approved
0.6509	Remote Similarity	NPD5223	Approved
0.6505	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4629	Approved
0.6505	Remote Similarity	NPD5210	Approved
0.6496	Remote Similarity	NPD7503	Approved
0.6495	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6274	Approved
0.6489	Remote Similarity	NPD6929	Approved
0.6484	Remote Similarity	NPD4058	Approved
0.6484	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5141	Approved
0.6466	Remote Similarity	NPD7100	Approved
0.6466	Remote Similarity	NPD7101	Approved
0.646	Remote Similarity	NPD6858	Approved
0.646	Remote Similarity	NPD4632	Approved
0.646	Remote Similarity	NPD7094	Approved
0.6458	Remote Similarity	NPD6435	Approved
0.6458	Remote Similarity	NPD4269	Approved
0.6458	Remote Similarity	NPD4270	Approved
0.6452	Remote Similarity	NPD6116	Phase 1
0.6449	Remote Similarity	NPD5225	Approved
0.6449	Remote Similarity	NPD5224	Approved
0.6449	Remote Similarity	NPD4633	Approved
0.6449	Remote Similarity	NPD5226	Approved
0.6444	Remote Similarity	NPD4243	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