NPASS Compound

Structure

NPC103088 OpenBabel07101718182D 36 38 0 0 1 0 0 0 0 0999 V2000 6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1587 -1.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7986 -2.7076 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 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 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 4.2072 0.3309 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 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 1 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 2.1369 -1.2213 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7767 -2.9155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8005 -0.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -0.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 1 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 -0.0000 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 1 0 0 0 0 0 0 0 0 0 2.0858 -3.8666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3005 -1.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 2.4459 -2.1723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 14 1 0 0 0 0 5 16 2 0 0 0 0 7 18 1 0 0 0 0 8 28 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 21 1 0 0 0 0 12 20 1 0 0 0 0 13 28 1 0 0 0 0 13 33 1 0 0 0 0 15 4 1 6 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 17 6 1 6 0 0 0 17 34 1 0 0 0 0 18 29 2 0 0 0 0 18 34 1 0 0 0 0 19 12 1 6 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 30 2 0 0 0 0 21 31 2 0 0 0 0 21 35 1 0 0 0 0 22 17 1 6 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 26 1 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 32 2 0 0 0 0 27 36 1 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.27
Volume:	521.678
LogP:	3.255
LogD:	2.054
LogS:	-3.819
# Rotatable Bonds:	12
TPSA:	108.5
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.153
Synthetic Accessibility Score:	5.298
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.75
MDCK Permeability:	9.323505219072104e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.311
Plasma Protein Binding (PPB):	65.05802154541016%
Volume Distribution (VD):	1.693
Pgp-substrate:	23.604019165039062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.225
CYP1A2-substrate:	0.144
CYP2C19-inhibitor:	0.651
CYP2C19-substrate:	0.629
CYP2C9-inhibitor:	0.847
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.914
CYP3A4-substrate:	0.435

ADMET: Excretion

Clearance (CL):	5.596
Half-life (T1/2):	0.709

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.93
Drug-inuced Liver Injury (DILI):	0.895
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.491
Maximum Recommended Daily Dose:	0.439
Skin Sensitization:	0.139
Carcinogencity:	0.141
Eye Corrosion:	0.08
Eye Irritation:	0.025
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC103088

Natural Product ID:	NPC103088
*Common Name:**	Abrotanifolon
IUPAC Name:	[(1S,3aR,5S,6R,7S,7aR)-1-[(1R)-1-acetyloxyethyl]-6-[(2S)-2-methylbutanoyl]oxy-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-3,3a,5,6,7,7a-hexahydro-1H-inden-5-yl] (E)-3-methylpent-2-enoate
Synonyms:
Standard InCHIKey:	RKAGQEAKHTWMEU-RXXFTBEBSA-N
Standard InCHI:	InChI=1S/C28H40O8/c1-9-14(3)11-21(31)35-25-16(5)19-12-20(30)22(17(6)34-18(7)29)23(19)24(28(8)13-33-28)26(25)36-27(32)15(4)10-2/h11,15,17,19,22-26H,5,9-10,12-13H2,1-4,6-8H3/b14-11+/t15-,17+,19-,22-,23-,24-,25-,26+,28+/m0/s1
SMILES:	CC[C@@H](C(=O)O[C@H]1[C@@H](OC(=O)/C=C(/CC)C)C(=C)[C@H]2[C@H]([C@@H]1[C@@]1(C)CO1)[C@@H]([C@H](OC(=O)C)C)C(=O)C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3298992
PubChem CID:	90683362
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO27190	Pittocaulon filare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24842703]
NPO27190	Pittocaulon filare	Species	Asteraceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.29	umol	PMID[511974]

☑ 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 NPC103088 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	256
0.1-0.2	1455
0.2-0.3	4572
0.3-0.4	7642
0.4-0.5	13740
0.5-0.6	7978
0.6-0.7	5417
0.7-0.8	1535
0.8-0.85	92
0.85-0.9	4
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470979
1.0	High Similarity	NPC470975
0.9417	High Similarity	NPC471933
0.9381	High Similarity	NPC471932
0.9126	High Similarity	NPC471934
0.86	High Similarity	NPC118159
0.8571	High Similarity	NPC474716
0.8559	High Similarity	NPC475520
0.8476	Intermediate Similarity	NPC470980
0.8468	Intermediate Similarity	NPC473720
0.8435	Intermediate Similarity	NPC473635
0.8393	Intermediate Similarity	NPC472667
0.8365	Intermediate Similarity	NPC475750
0.8365	Intermediate Similarity	NPC470972
0.8333	Intermediate Similarity	NPC253906
0.8333	Intermediate Similarity	NPC170538
0.8319	Intermediate Similarity	NPC4548
0.8319	Intermediate Similarity	NPC251226
0.8304	Intermediate Similarity	NPC470420
0.8288	Intermediate Similarity	NPC470793
0.8276	Intermediate Similarity	NPC293112
0.8273	Intermediate Similarity	NPC470120
0.8261	Intermediate Similarity	NPC473802
0.8261	Intermediate Similarity	NPC469789
0.8261	Intermediate Similarity	NPC11895
0.8246	Intermediate Similarity	NPC310511
0.8246	Intermediate Similarity	NPC159456
0.8246	Intermediate Similarity	NPC4021
0.8241	Intermediate Similarity	NPC469370
0.8224	Intermediate Similarity	NPC180744
0.8224	Intermediate Similarity	NPC475587
0.8224	Intermediate Similarity	NPC475510
0.8224	Intermediate Similarity	NPC469558
0.8205	Intermediate Similarity	NPC42399
0.819	Intermediate Similarity	NPC473709
0.819	Intermediate Similarity	NPC473919
0.8174	Intermediate Similarity	NPC23786
0.8174	Intermediate Similarity	NPC470265
0.8174	Intermediate Similarity	NPC269642
0.8173	Intermediate Similarity	NPC469551
0.8158	Intermediate Similarity	NPC268530
0.8158	Intermediate Similarity	NPC143755
0.8158	Intermediate Similarity	NPC154491
0.8148	Intermediate Similarity	NPC473939
0.8148	Intermediate Similarity	NPC94377
0.8148	Intermediate Similarity	NPC473595
0.812	Intermediate Similarity	NPC471939
0.8103	Intermediate Similarity	NPC472399
0.81	Intermediate Similarity	NPC475748
0.8091	Intermediate Similarity	NPC475495
0.8091	Intermediate Similarity	NPC194619
0.8087	Intermediate Similarity	NPC67569
0.8087	Intermediate Similarity	NPC204731
0.8073	Intermediate Similarity	NPC273433
0.807	Intermediate Similarity	NPC470186
0.807	Intermediate Similarity	NPC42673
0.8053	Intermediate Similarity	NPC469684
0.8051	Intermediate Similarity	NPC471940
0.8051	Intermediate Similarity	NPC287423
0.8051	Intermediate Similarity	NPC298841
0.8036	Intermediate Similarity	NPC238667
0.8034	Intermediate Similarity	NPC8369
0.8034	Intermediate Similarity	NPC469790
0.8034	Intermediate Similarity	NPC81736
0.8034	Intermediate Similarity	NPC172154
0.8018	Intermediate Similarity	NPC475277
0.8018	Intermediate Similarity	NPC477093
0.8018	Intermediate Similarity	NPC473522
0.8	Intermediate Similarity	NPC473594
0.8	Intermediate Similarity	NPC472214
0.8	Intermediate Similarity	NPC281624
0.8	Intermediate Similarity	NPC473975
0.8	Intermediate Similarity	NPC472004
0.8	Intermediate Similarity	NPC474586
0.8	Intermediate Similarity	NPC472215
0.8	Intermediate Similarity	NPC473843
0.7983	Intermediate Similarity	NPC473620
0.7966	Intermediate Similarity	NPC120994
0.7966	Intermediate Similarity	NPC203702
0.7966	Intermediate Similarity	NPC470973
0.7965	Intermediate Similarity	NPC476710
0.7965	Intermediate Similarity	NPC234858
0.7965	Intermediate Similarity	NPC477509
0.7965	Intermediate Similarity	NPC471127
0.7965	Intermediate Similarity	NPC476711
0.7965	Intermediate Similarity	NPC154363
0.7961	Intermediate Similarity	NPC470978
0.7961	Intermediate Similarity	NPC470974
0.7946	Intermediate Similarity	NPC477126
0.7944	Intermediate Similarity	NPC474166
0.7944	Intermediate Similarity	NPC19239
0.7931	Intermediate Similarity	NPC472401
0.7931	Intermediate Similarity	NPC46570
0.7928	Intermediate Similarity	NPC469655
0.7928	Intermediate Similarity	NPC470960
0.7928	Intermediate Similarity	NPC474846
0.7928	Intermediate Similarity	NPC469656
0.7917	Intermediate Similarity	NPC175186
0.7917	Intermediate Similarity	NPC231529
0.7917	Intermediate Similarity	NPC472770
0.7913	Intermediate Similarity	NPC476960
0.7913	Intermediate Similarity	NPC5292
0.7913	Intermediate Similarity	NPC475041
0.7905	Intermediate Similarity	NPC264378
0.7895	Intermediate Similarity	NPC10721
0.7895	Intermediate Similarity	NPC476712
0.7895	Intermediate Similarity	NPC53396
0.7895	Intermediate Similarity	NPC476713
0.7895	Intermediate Similarity	NPC474518
0.7895	Intermediate Similarity	NPC58662
0.7895	Intermediate Similarity	NPC98249
0.7895	Intermediate Similarity	NPC55296
0.7895	Intermediate Similarity	NPC473656
0.789	Intermediate Similarity	NPC471601
0.7879	Intermediate Similarity	NPC474045
0.7879	Intermediate Similarity	NPC469676
0.7879	Intermediate Similarity	NPC261253
0.7876	Intermediate Similarity	NPC284915
0.7876	Intermediate Similarity	NPC178289
0.7876	Intermediate Similarity	NPC73314
0.7876	Intermediate Similarity	NPC90472
0.7864	Intermediate Similarity	NPC476716
0.7863	Intermediate Similarity	NPC19464
0.7863	Intermediate Similarity	NPC107493
0.7857	Intermediate Similarity	NPC473877
0.7857	Intermediate Similarity	NPC222834
0.7857	Intermediate Similarity	NPC317687
0.7857	Intermediate Similarity	NPC269530
0.7851	Intermediate Similarity	NPC471170
0.7851	Intermediate Similarity	NPC475389
0.7851	Intermediate Similarity	NPC473838
0.785	Intermediate Similarity	NPC105725
0.785	Intermediate Similarity	NPC474709
0.7845	Intermediate Similarity	NPC475003
0.7845	Intermediate Similarity	NPC157252
0.7845	Intermediate Similarity	NPC145182
0.7845	Intermediate Similarity	NPC476961
0.7845	Intermediate Similarity	NPC471128
0.7845	Intermediate Similarity	NPC471126
0.7843	Intermediate Similarity	NPC207641
0.7843	Intermediate Similarity	NPC472953
0.7843	Intermediate Similarity	NPC221282
0.7843	Intermediate Similarity	NPC233437
0.7833	Intermediate Similarity	NPC236999
0.7833	Intermediate Similarity	NPC311534
0.7826	Intermediate Similarity	NPC709
0.7826	Intermediate Similarity	NPC146280
0.7826	Intermediate Similarity	NPC284707
0.7826	Intermediate Similarity	NPC159928
0.7826	Intermediate Similarity	NPC50774
0.7826	Intermediate Similarity	NPC475372
0.7826	Intermediate Similarity	NPC153440
0.7826	Intermediate Similarity	NPC124676
0.7818	Intermediate Similarity	NPC318363
0.7818	Intermediate Similarity	NPC475418
0.7818	Intermediate Similarity	NPC472439
0.7818	Intermediate Similarity	NPC469916
0.7818	Intermediate Similarity	NPC473482
0.781	Intermediate Similarity	NPC100912
0.7807	Intermediate Similarity	NPC190286
0.78	Intermediate Similarity	NPC231889
0.7797	Intermediate Similarity	NPC120724
0.7797	Intermediate Similarity	NPC204812
0.7788	Intermediate Similarity	NPC962
0.7788	Intermediate Similarity	NPC473535
0.7788	Intermediate Similarity	NPC159333
0.7788	Intermediate Similarity	NPC250109
0.7788	Intermediate Similarity	NPC472757
0.7788	Intermediate Similarity	NPC33360
0.7788	Intermediate Similarity	NPC471204
0.7788	Intermediate Similarity	NPC317210
0.7787	Intermediate Similarity	NPC472769
0.7787	Intermediate Similarity	NPC475139
0.7787	Intermediate Similarity	NPC180902
0.7778	Intermediate Similarity	NPC52839
0.7769	Intermediate Similarity	NPC104382
0.7769	Intermediate Similarity	NPC470851
0.7769	Intermediate Similarity	NPC475371
0.7768	Intermediate Similarity	NPC317107
0.7759	Intermediate Similarity	NPC270850
0.7759	Intermediate Similarity	NPC236918
0.7759	Intermediate Similarity	NPC156745
0.7759	Intermediate Similarity	NPC230513
0.7759	Intermediate Similarity	NPC77689
0.7759	Intermediate Similarity	NPC312536
0.7759	Intermediate Similarity	NPC473839
0.7759	Intermediate Similarity	NPC473203
0.7759	Intermediate Similarity	NPC305260
0.7759	Intermediate Similarity	NPC211093
0.7759	Intermediate Similarity	NPC473636
0.7757	Intermediate Similarity	NPC475099
0.7757	Intermediate Similarity	NPC264477
0.7757	Intermediate Similarity	NPC477511
0.7748	Intermediate Similarity	NPC475065
0.7748	Intermediate Similarity	NPC42662
0.7745	Intermediate Similarity	NPC161638
0.7739	Intermediate Similarity	NPC475809
0.7739	Intermediate Similarity	NPC478204
0.7739	Intermediate Similarity	NPC286528
0.7739	Intermediate Similarity	NPC20302

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 NPC103088 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	1874
0.2-0.3	3766
0.3-0.4	2133
0.4-0.5	713
0.5-0.6	249
0.6-0.7	182
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7798	Intermediate Similarity	NPD6008	Approved
0.7739	Intermediate Similarity	NPD7115	Discovery
0.7573	Intermediate Similarity	NPD6698	Approved
0.7573	Intermediate Similarity	NPD46	Approved
0.7568	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6648	Approved
0.748	Intermediate Similarity	NPD7319	Approved
0.7431	Intermediate Similarity	NPD5344	Discontinued
0.7395	Intermediate Similarity	NPD6319	Approved
0.7377	Intermediate Similarity	NPD7507	Approved
0.7368	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7638	Approved
0.7241	Intermediate Similarity	NPD8297	Approved
0.7241	Intermediate Similarity	NPD6053	Discontinued
0.7217	Intermediate Similarity	NPD6371	Approved
0.7182	Intermediate Similarity	NPD7640	Approved
0.7182	Intermediate Similarity	NPD7639	Approved
0.7168	Intermediate Similarity	NPD5739	Approved
0.7168	Intermediate Similarity	NPD6402	Approved
0.7168	Intermediate Similarity	NPD7128	Approved
0.7168	Intermediate Similarity	NPD6675	Approved
0.7154	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD1695	Approved
0.713	Intermediate Similarity	NPD6372	Approved
0.713	Intermediate Similarity	NPD6373	Approved
0.7107	Intermediate Similarity	NPD6059	Approved
0.7107	Intermediate Similarity	NPD6054	Approved
0.7097	Intermediate Similarity	NPD6616	Approved
0.7091	Intermediate Similarity	NPD4225	Approved
0.7043	Intermediate Similarity	NPD6881	Approved
0.7043	Intermediate Similarity	NPD6686	Approved
0.7043	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7320	Approved
0.7043	Intermediate Similarity	NPD6899	Approved
0.704	Intermediate Similarity	NPD8293	Discontinued
0.704	Intermediate Similarity	NPD7078	Approved
0.7034	Intermediate Similarity	NPD4632	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD7983	Approved
0.7009	Intermediate Similarity	NPD6649	Approved
0.6992	Remote Similarity	NPD6370	Approved
0.6984	Remote Similarity	NPD7736	Approved
0.6957	Remote Similarity	NPD5701	Approved
0.6957	Remote Similarity	NPD5697	Approved
0.6949	Remote Similarity	NPD6882	Approved
0.6944	Remote Similarity	NPD5779	Approved
0.6944	Remote Similarity	NPD5778	Approved
0.6935	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD7838	Discovery
0.6911	Remote Similarity	NPD6016	Approved
0.6911	Remote Similarity	NPD6015	Approved
0.6885	Remote Similarity	NPD7516	Approved
0.6864	Remote Similarity	NPD8130	Phase 1
0.6864	Remote Similarity	NPD6847	Approved
0.6864	Remote Similarity	NPD6617	Approved
0.6864	Remote Similarity	NPD6869	Approved
0.686	Remote Similarity	NPD6009	Approved
0.6855	Remote Similarity	NPD5988	Approved
0.6838	Remote Similarity	NPD6012	Approved
0.6838	Remote Similarity	NPD6013	Approved
0.6838	Remote Similarity	NPD6014	Approved
0.6818	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7327	Approved
0.6803	Remote Similarity	NPD7328	Approved
0.6796	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6399	Phase 3
0.678	Remote Similarity	NPD4634	Approved
0.6774	Remote Similarity	NPD8516	Approved
0.6774	Remote Similarity	NPD8033	Approved
0.6774	Remote Similarity	NPD5983	Phase 2
0.6774	Remote Similarity	NPD8517	Approved
0.6774	Remote Similarity	NPD8513	Phase 3
0.6774	Remote Similarity	NPD8515	Approved
0.6752	Remote Similarity	NPD6011	Approved
0.6729	Remote Similarity	NPD6672	Approved
0.6729	Remote Similarity	NPD5737	Approved
0.6723	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6409	Approved
0.6698	Remote Similarity	NPD7334	Approved
0.6698	Remote Similarity	NPD6684	Approved
0.6698	Remote Similarity	NPD7146	Approved
0.6698	Remote Similarity	NPD5330	Approved
0.6698	Remote Similarity	NPD7521	Approved
0.6697	Remote Similarity	NPD5693	Phase 1
0.6696	Remote Similarity	NPD4755	Approved
0.6694	Remote Similarity	NPD8377	Approved
0.6694	Remote Similarity	NPD8294	Approved
0.6693	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.664	Remote Similarity	NPD8379	Approved
0.664	Remote Similarity	NPD8378	Approved
0.664	Remote Similarity	NPD8335	Approved
0.664	Remote Similarity	NPD8296	Approved
0.664	Remote Similarity	NPD8380	Approved
0.6609	Remote Similarity	NPD5211	Phase 2
0.6609	Remote Similarity	NPD7632	Discontinued
0.6606	Remote Similarity	NPD5785	Approved
0.6604	Remote Similarity	NPD1694	Approved
0.6589	Remote Similarity	NPD6033	Approved
0.6579	Remote Similarity	NPD5286	Approved
0.6579	Remote Similarity	NPD4696	Approved
0.6579	Remote Similarity	NPD5285	Approved
0.6579	Remote Similarity	NPD4700	Approved
0.6577	Remote Similarity	NPD7900	Approved
0.6577	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6903	Approved
0.6565	Remote Similarity	NPD7260	Phase 2
0.6549	Remote Similarity	NPD6083	Phase 2
0.6549	Remote Similarity	NPD6084	Phase 2
0.6545	Remote Similarity	NPD6079	Approved
0.6545	Remote Similarity	NPD7637	Suspended
0.6542	Remote Similarity	NPD5786	Approved
0.6525	Remote Similarity	NPD6412	Phase 2
0.6518	Remote Similarity	NPD5695	Phase 3
0.6515	Remote Similarity	NPD8338	Approved
0.6514	Remote Similarity	NPD6673	Approved
0.6514	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6080	Approved
0.6514	Remote Similarity	NPD6101	Approved
0.6514	Remote Similarity	NPD6904	Approved
0.6512	Remote Similarity	NPD8074	Phase 3
0.6508	Remote Similarity	NPD7503	Approved
0.6508	Remote Similarity	NPD6921	Approved
0.6504	Remote Similarity	NPD6274	Approved
0.6496	Remote Similarity	NPD5141	Approved
0.6481	Remote Similarity	NPD3573	Approved
0.648	Remote Similarity	NPD7100	Approved
0.648	Remote Similarity	NPD7101	Approved
0.6476	Remote Similarity	NPD6435	Approved
0.6475	Remote Similarity	NPD8133	Approved
0.6466	Remote Similarity	NPD4633	Approved
0.6466	Remote Similarity	NPD5225	Approved
0.6466	Remote Similarity	NPD5226	Approved
0.6466	Remote Similarity	NPD5224	Approved
0.6449	Remote Similarity	NPD5363	Approved
0.6441	Remote Similarity	NPD4768	Approved
0.6441	Remote Similarity	NPD4767	Approved
0.6429	Remote Similarity	NPD5282	Discontinued
0.6429	Remote Similarity	NPD6001	Approved
0.6429	Remote Similarity	NPD7748	Approved
0.641	Remote Similarity	NPD5174	Approved
0.641	Remote Similarity	NPD5175	Approved
0.6406	Remote Similarity	NPD7642	Approved
0.6404	Remote Similarity	NPD7902	Approved
0.64	Remote Similarity	NPD6335	Approved
0.6396	Remote Similarity	NPD6411	Approved
0.6396	Remote Similarity	NPD6050	Approved
0.6381	Remote Similarity	NPD5369	Approved
0.6379	Remote Similarity	NPD5223	Approved
0.6379	Remote Similarity	NPD1700	Approved
0.6378	Remote Similarity	NPD6908	Approved
0.6378	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD6051	Approved
0.6348	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5696	Approved
0.6339	Remote Similarity	NPD4202	Approved
0.6336	Remote Similarity	NPD8336	Approved
0.6336	Remote Similarity	NPD8337	Approved
0.6333	Remote Similarity	NPD4730	Approved
0.6333	Remote Similarity	NPD4729	Approved
0.6321	Remote Similarity	NPD4270	Approved
0.6321	Remote Similarity	NPD4269	Approved
0.6321	Remote Similarity	NPD5209	Approved
0.632	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6317	Approved
0.6316	Remote Similarity	NPD5222	Approved
0.6316	Remote Similarity	NPD7839	Suspended
0.6316	Remote Similarity	NPD4697	Phase 3
0.6316	Remote Similarity	NPD5221	Approved
0.6316	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD3168	Discontinued
0.6306	Remote Similarity	NPD5692	Phase 3
0.6286	Remote Similarity	NPD5368	Approved
0.6281	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7829	Approved
0.6279	Remote Similarity	NPD7830	Approved
0.6273	Remote Similarity	NPD5208	Approved
0.6271	Remote Similarity	NPD4754	Approved
0.627	Remote Similarity	NPD6313	Approved
0.627	Remote Similarity	NPD6314	Approved
0.6269	Remote Similarity	NPD6845	Suspended
0.6262	Remote Similarity	NPD5362	Discontinued
0.6261	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD8034	Phase 2
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD5694	Approved
0.625	Remote Similarity	NPD8035	Phase 2
0.624	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD6098	Approved
0.6239	Remote Similarity	NPD3618	Phase 1

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