NPASS Compound

Structure

NPC159333 OpenBabel07101718272D 36 39 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -4.8660 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 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 0.8660 -2.5000 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 -3.5000 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 -2.5000 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 1.7321 -2.0000 0.0000 C 0 0 0 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 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -4.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 1 16 2 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 25 1 0 0 0 0 10 27 1 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 13 26 1 0 0 0 0 14 22 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 35 1 0 0 0 0 16 18 1 0 0 0 0 17 23 1 0 0 0 0 18 27 1 1 0 0 0 19 25 1 0 0 0 0 19 27 1 1 0 0 0 20 28 1 0 0 0 0 20 29 2 0 0 0 0 21 30 2 0 0 0 0 21 31 1 0 0 0 0 22 32 2 0 0 0 0 22 35 1 0 0 0 0 23 24 1 0 0 0 0 23 33 2 0 0 0 0 24 28 1 1 0 0 0 24 36 1 0 0 0 0 26 4 1 6 0 0 0 26 34 1 0 0 0 0 27 5 1 1 0 0 0 28 12 1 1 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.26
Volume:	513.121
LogP:	3.57
LogD:	1.955
LogS:	-4.137
# Rotatable Bonds:	8
TPSA:	130.5
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	5.224
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:	-5.456
MDCK Permeability:	2.117125222866889e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.086
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.252
Plasma Protein Binding (PPB):	60.031150817871094%
Volume Distribution (VD):	0.353
Pgp-substrate:	41.39398193359375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.255
CYP2C9-inhibitor:	0.126
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	9.783
Half-life (T1/2):	0.738

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.596
AMES Toxicity:	0.968
Rat Oral Acute Toxicity:	0.515
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.595
Carcinogencity:	0.922
Eye Corrosion:	0.212
Eye Irritation:	0.016
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC159333

Natural Product ID:	NPC159333
*Common Name:**	4'-Oxomacrophorin D
IUPAC Name:	(3S)-5-[[(1S,6R)-6-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
Synonyms:	4'-Oxomacrophorin D
Standard InCHIKey:	TZHODXJMZGQSQM-PWMRZZKKSA-N
Standard InCHI:	InChI=1S/C28H38O8/c1-16-7-8-19-25(2,3)9-6-10-27(19,5)18(16)12-28-20(29)11-17(23(33)24(28)36-28)15-35-22(32)14-26(4,34)13-21(30)31/h11,18-19,24,34H,1,6-10,12-15H2,2-5H3,(H,30,31)/t18-,19-,24+,26-,27+,28-/m0/s1
SMILES:	OC(=O)C[C@@](CC(=O)OCC1=CC(=O)[C@]2([C@@H](C1=O)O2)C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464640
PubChem CID:	11005626
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0001989] Heterocyclic fatty acids

*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
NPO32585	eupenicillium crustaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575965]

☑ 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
IC50	2
Others	1

Activity Type	# Activity
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.5	ug.mL-1	PMID[493412]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.0	ug.mL-1	PMID[493412]
NPT2	Others	Unspecified		Ratio IC50	=	2.0	n.a.	PMID[493412]

☑ 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 NPC159333 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	247
0.1-0.2	1434
0.2-0.3	4349
0.3-0.4	7827
0.4-0.5	13055
0.5-0.6	7787
0.6-0.7	6140
0.7-0.8	1807
0.8-0.85	42
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8972	High Similarity	NPC322903
0.8818	High Similarity	NPC317687
0.8774	High Similarity	NPC131366
0.8727	High Similarity	NPC317107
0.8584	High Similarity	NPC270478
0.8571	High Similarity	NPC264378
0.8482	Intermediate Similarity	NPC277769
0.8475	Intermediate Similarity	NPC24651
0.8475	Intermediate Similarity	NPC470922
0.8417	Intermediate Similarity	NPC476859
0.8411	Intermediate Similarity	NPC207885
0.8407	Intermediate Similarity	NPC477126
0.839	Intermediate Similarity	NPC265557
0.839	Intermediate Similarity	NPC18945
0.839	Intermediate Similarity	NPC67251
0.839	Intermediate Similarity	NPC91693
0.839	Intermediate Similarity	NPC105926
0.839	Intermediate Similarity	NPC120724
0.8378	Intermediate Similarity	NPC87335
0.8362	Intermediate Similarity	NPC472933
0.8361	Intermediate Similarity	NPC476193
0.8348	Intermediate Similarity	NPC239273
0.8348	Intermediate Similarity	NPC134430
0.8348	Intermediate Similarity	NPC243065
0.8348	Intermediate Similarity	NPC472934
0.8319	Intermediate Similarity	NPC90952
0.8319	Intermediate Similarity	NPC269530
0.8319	Intermediate Similarity	NPC4573
0.8319	Intermediate Similarity	NPC476729
0.8305	Intermediate Similarity	NPC312833
0.8305	Intermediate Similarity	NPC470265
0.8305	Intermediate Similarity	NPC23786
0.8291	Intermediate Similarity	NPC107338
0.8291	Intermediate Similarity	NPC109607
0.8288	Intermediate Similarity	NPC476479
0.8279	Intermediate Similarity	NPC476855
0.8279	Intermediate Similarity	NPC476852
0.8273	Intermediate Similarity	NPC1679
0.8257	Intermediate Similarity	NPC95899
0.825	Intermediate Similarity	NPC473635
0.8246	Intermediate Similarity	NPC25909
0.8246	Intermediate Similarity	NPC471204
0.8246	Intermediate Similarity	NPC472926
0.8241	Intermediate Similarity	NPC112613
0.8235	Intermediate Similarity	NPC469789
0.823	Intermediate Similarity	NPC34315
0.822	Intermediate Similarity	NPC67569
0.822	Intermediate Similarity	NPC470779
0.8208	Intermediate Similarity	NPC94337
0.8205	Intermediate Similarity	NPC476960
0.8205	Intermediate Similarity	NPC475775
0.8205	Intermediate Similarity	NPC476529
0.8205	Intermediate Similarity	NPC473636
0.8205	Intermediate Similarity	NPC77689
0.8197	Intermediate Similarity	NPC476851
0.8197	Intermediate Similarity	NPC476854
0.819	Intermediate Similarity	NPC475809
0.819	Intermediate Similarity	NPC472927
0.819	Intermediate Similarity	NPC476415
0.8182	Intermediate Similarity	NPC42399
0.8165	Intermediate Similarity	NPC162973
0.8158	Intermediate Similarity	NPC475391
0.8151	Intermediate Similarity	NPC170538
0.8148	Intermediate Similarity	NPC472972
0.8148	Intermediate Similarity	NPC471413
0.8148	Intermediate Similarity	NPC469551
0.8145	Intermediate Similarity	NPC58029
0.8142	Intermediate Similarity	NPC253906
0.8131	Intermediate Similarity	NPC471916
0.813	Intermediate Similarity	NPC476863
0.813	Intermediate Similarity	NPC476862
0.8125	Intermediate Similarity	NPC476802
0.8125	Intermediate Similarity	NPC89171
0.8125	Intermediate Similarity	NPC275539
0.8125	Intermediate Similarity	NPC151393
0.8125	Intermediate Similarity	NPC189075
0.812	Intermediate Similarity	NPC21326
0.812	Intermediate Similarity	NPC240509
0.812	Intermediate Similarity	NPC297179
0.812	Intermediate Similarity	NPC251310
0.812	Intermediate Similarity	NPC17772
0.8108	Intermediate Similarity	NPC284365
0.8108	Intermediate Similarity	NPC123726
0.8103	Intermediate Similarity	NPC148458
0.8099	Intermediate Similarity	NPC293112
0.8091	Intermediate Similarity	NPC478057
0.8087	Intermediate Similarity	NPC7921
0.8087	Intermediate Similarity	NPC474937
0.8087	Intermediate Similarity	NPC472929
0.8087	Intermediate Similarity	NPC208998
0.8087	Intermediate Similarity	NPC122056
0.8083	Intermediate Similarity	NPC11895
0.8083	Intermediate Similarity	NPC204812
0.8073	Intermediate Similarity	NPC476478
0.8073	Intermediate Similarity	NPC323441
0.8073	Intermediate Similarity	NPC471412
0.807	Intermediate Similarity	NPC96739
0.807	Intermediate Similarity	NPC174471
0.807	Intermediate Similarity	NPC146945
0.807	Intermediate Similarity	NPC260786
0.807	Intermediate Similarity	NPC474871
0.807	Intermediate Similarity	NPC171888
0.8065	Intermediate Similarity	NPC34963
0.8056	Intermediate Similarity	NPC316598
0.8053	Intermediate Similarity	NPC474242
0.8053	Intermediate Similarity	NPC250018
0.8053	Intermediate Similarity	NPC475922
0.8051	Intermediate Similarity	NPC473839
0.8051	Intermediate Similarity	NPC211093
0.8051	Intermediate Similarity	NPC268958
0.8051	Intermediate Similarity	NPC475520
0.8051	Intermediate Similarity	NPC470777
0.8036	Intermediate Similarity	NPC475294
0.8036	Intermediate Similarity	NPC110496
0.8036	Intermediate Similarity	NPC474716
0.8034	Intermediate Similarity	NPC473590
0.8034	Intermediate Similarity	NPC469684
0.8033	Intermediate Similarity	NPC287423
0.8033	Intermediate Similarity	NPC298841
0.8019	Intermediate Similarity	NPC477439
0.8019	Intermediate Similarity	NPC470697
0.8017	Intermediate Similarity	NPC32868
0.8017	Intermediate Similarity	NPC8369
0.8017	Intermediate Similarity	NPC241456
0.8017	Intermediate Similarity	NPC238667
0.8017	Intermediate Similarity	NPC81736
0.8017	Intermediate Similarity	NPC473798
0.8017	Intermediate Similarity	NPC172154
0.8017	Intermediate Similarity	NPC474872
0.8	Intermediate Similarity	NPC476081
0.8	Intermediate Similarity	NPC265499
0.8	Intermediate Similarity	NPC264634
0.8	Intermediate Similarity	NPC101825
0.8	Intermediate Similarity	NPC147180
0.8	Intermediate Similarity	NPC151216
0.8	Intermediate Similarity	NPC100267
0.8	Intermediate Similarity	NPC89227
0.8	Intermediate Similarity	NPC17138
0.8	Intermediate Similarity	NPC475038
0.8	Intermediate Similarity	NPC170212
0.8	Intermediate Similarity	NPC109195
0.8	Intermediate Similarity	NPC473877
0.8	Intermediate Similarity	NPC40918
0.8	Intermediate Similarity	NPC475524
0.8	Intermediate Similarity	NPC469673
0.8	Intermediate Similarity	NPC221511
0.8	Intermediate Similarity	NPC215643
0.8	Intermediate Similarity	NPC193948
0.7984	Intermediate Similarity	NPC279478
0.7984	Intermediate Similarity	NPC241935
0.7982	Intermediate Similarity	NPC161816
0.7982	Intermediate Similarity	NPC115257
0.7982	Intermediate Similarity	NPC174314
0.7982	Intermediate Similarity	NPC474012
0.7982	Intermediate Similarity	NPC476299
0.7982	Intermediate Similarity	NPC54705
0.7982	Intermediate Similarity	NPC476933
0.7967	Intermediate Similarity	NPC473620
0.7966	Intermediate Similarity	NPC470776
0.7966	Intermediate Similarity	NPC473720
0.7966	Intermediate Similarity	NPC470420
0.7966	Intermediate Similarity	NPC118638
0.7966	Intermediate Similarity	NPC50774
0.7966	Intermediate Similarity	NPC709
0.7965	Intermediate Similarity	NPC293850
0.7965	Intermediate Similarity	NPC473483
0.7965	Intermediate Similarity	NPC472439
0.7965	Intermediate Similarity	NPC469916
0.7963	Intermediate Similarity	NPC170131
0.7951	Intermediate Similarity	NPC225049
0.7949	Intermediate Similarity	NPC270958
0.7949	Intermediate Similarity	NPC213084
0.7949	Intermediate Similarity	NPC96312
0.7949	Intermediate Similarity	NPC40632
0.7949	Intermediate Similarity	NPC476710
0.7949	Intermediate Similarity	NPC190185
0.7949	Intermediate Similarity	NPC235539
0.7949	Intermediate Similarity	NPC152199
0.7949	Intermediate Similarity	NPC477509
0.7949	Intermediate Similarity	NPC251236
0.7949	Intermediate Similarity	NPC134869
0.7949	Intermediate Similarity	NPC328374
0.7949	Intermediate Similarity	NPC207217
0.7949	Intermediate Similarity	NPC476711
0.7946	Intermediate Similarity	NPC111952
0.7946	Intermediate Similarity	NPC472935
0.7944	Intermediate Similarity	NPC477438
0.7944	Intermediate Similarity	NPC477437
0.7944	Intermediate Similarity	NPC37603
0.7944	Intermediate Similarity	NPC471786
0.7937	Intermediate Similarity	NPC476823
0.7934	Intermediate Similarity	NPC472399
0.7931	Intermediate Similarity	NPC202889
0.7931	Intermediate Similarity	NPC33360
0.7931	Intermediate Similarity	NPC71889
0.7931	Intermediate Similarity	NPC198539
0.7931	Intermediate Similarity	NPC94509
0.7931	Intermediate Similarity	NPC321496
0.7928	Intermediate Similarity	NPC275583
0.7928	Intermediate Similarity	NPC474166

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 NPC159333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1630
0.2-0.3	3630
0.3-0.4	2327
0.4-0.5	848
0.5-0.6	259
0.6-0.7	191
0.7-0.8	49
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
0.7913	Intermediate Similarity	NPD6649	Approved
0.7913	Intermediate Similarity	NPD6650	Approved
0.7895	Intermediate Similarity	NPD6373	Approved
0.7895	Intermediate Similarity	NPD6372	Approved
0.7881	Intermediate Similarity	NPD7115	Discovery
0.7833	Intermediate Similarity	NPD6319	Approved
0.7826	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD6881	Approved
0.7807	Intermediate Similarity	NPD6899	Approved
0.7788	Intermediate Similarity	NPD7128	Approved
0.7788	Intermediate Similarity	NPD5739	Approved
0.7788	Intermediate Similarity	NPD6675	Approved
0.7788	Intermediate Similarity	NPD6402	Approved
0.7719	Intermediate Similarity	NPD5697	Approved
0.7692	Intermediate Similarity	NPD6882	Approved
0.7692	Intermediate Similarity	NPD8297	Approved
0.7672	Intermediate Similarity	NPD7102	Approved
0.7672	Intermediate Similarity	NPD6883	Approved
0.7672	Intermediate Similarity	NPD7290	Approved
0.7652	Intermediate Similarity	NPD7320	Approved
0.7607	Intermediate Similarity	NPD8130	Phase 1
0.7607	Intermediate Similarity	NPD6617	Approved
0.7607	Intermediate Similarity	NPD6869	Approved
0.7607	Intermediate Similarity	NPD6847	Approved
0.7586	Intermediate Similarity	NPD6012	Approved
0.7586	Intermediate Similarity	NPD6013	Approved
0.7586	Intermediate Similarity	NPD6014	Approved
0.7586	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7492	Approved
0.7568	Intermediate Similarity	NPD7638	Approved
0.7565	Intermediate Similarity	NPD5701	Approved
0.7565	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6054	Approved
0.752	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7478	Intermediate Similarity	NPD6008	Approved
0.7477	Intermediate Similarity	NPD6084	Phase 2
0.7477	Intermediate Similarity	NPD7902	Approved
0.7477	Intermediate Similarity	NPD6083	Phase 2
0.746	Intermediate Similarity	NPD7078	Approved
0.7431	Intermediate Similarity	NPD6399	Phase 3
0.7419	Intermediate Similarity	NPD6370	Approved
0.7411	Intermediate Similarity	NPD5696	Approved
0.7402	Intermediate Similarity	NPD7736	Approved
0.7398	Intermediate Similarity	NPD6059	Approved
0.7364	Intermediate Similarity	NPD7748	Approved
0.736	Intermediate Similarity	NPD7604	Phase 2
0.7339	Intermediate Similarity	NPD6016	Approved
0.7339	Intermediate Similarity	NPD6015	Approved
0.7333	Intermediate Similarity	NPD4632	Approved
0.7323	Intermediate Similarity	NPD8293	Discontinued
0.7311	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5695	Phase 3
0.7295	Intermediate Similarity	NPD6009	Approved
0.728	Intermediate Similarity	NPD5988	Approved
0.7257	Intermediate Similarity	NPD4225	Approved
0.7248	Intermediate Similarity	NPD6698	Approved
0.7248	Intermediate Similarity	NPD46	Approved
0.7227	Intermediate Similarity	NPD4634	Approved
0.7222	Intermediate Similarity	NPD6672	Approved
0.7222	Intermediate Similarity	NPD5737	Approved
0.7217	Intermediate Similarity	NPD5211	Phase 2
0.7213	Intermediate Similarity	NPD6274	Approved
0.7209	Intermediate Similarity	NPD7319	Approved
0.7207	Intermediate Similarity	NPD7900	Approved
0.7207	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5983	Phase 2
0.7193	Intermediate Similarity	NPD4696	Approved
0.7193	Intermediate Similarity	NPD5285	Approved
0.7193	Intermediate Similarity	NPD5286	Approved
0.7182	Intermediate Similarity	NPD5693	Phase 1
0.7182	Intermediate Similarity	NPD7515	Phase 2
0.7177	Intermediate Similarity	NPD7101	Approved
0.7177	Intermediate Similarity	NPD7100	Approved
0.7168	Intermediate Similarity	NPD4755	Approved
0.7154	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5779	Approved
0.7117	Intermediate Similarity	NPD5778	Approved
0.7109	Intermediate Similarity	NPD6336	Discontinued
0.7109	Intermediate Similarity	NPD7507	Approved
0.7107	Intermediate Similarity	NPD6053	Discontinued
0.7097	Intermediate Similarity	NPD6335	Approved
0.7094	Intermediate Similarity	NPD5141	Approved
0.7083	Intermediate Similarity	NPD6371	Approved
0.7069	Intermediate Similarity	NPD5226	Approved
0.7069	Intermediate Similarity	NPD5224	Approved
0.7069	Intermediate Similarity	NPD5225	Approved
0.7069	Intermediate Similarity	NPD4633	Approved
0.7043	Intermediate Similarity	NPD4700	Approved
0.7027	Intermediate Similarity	NPD6411	Approved
0.7016	Intermediate Similarity	NPD6317	Approved
0.7009	Intermediate Similarity	NPD5174	Approved
0.7009	Intermediate Similarity	NPD5175	Approved
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6080	Approved
0.6983	Remote Similarity	NPD5344	Discontinued
0.6983	Remote Similarity	NPD5223	Approved
0.6981	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3573	Approved
0.697	Remote Similarity	NPD7260	Phase 2
0.696	Remote Similarity	NPD6314	Approved
0.696	Remote Similarity	NPD6313	Approved
0.6952	Remote Similarity	NPD4695	Discontinued
0.6935	Remote Similarity	NPD6868	Approved
0.693	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4697	Phase 3
0.693	Remote Similarity	NPD5221	Approved
0.693	Remote Similarity	NPD5222	Approved
0.6929	Remote Similarity	NPD6908	Approved
0.6929	Remote Similarity	NPD6921	Approved
0.6929	Remote Similarity	NPD6909	Approved
0.6923	Remote Similarity	NPD7632	Discontinued
0.6917	Remote Similarity	NPD4730	Approved
0.6917	Remote Similarity	NPD4729	Approved
0.6903	Remote Similarity	NPD5282	Discontinued
0.6897	Remote Similarity	NPD6648	Approved
0.6891	Remote Similarity	NPD4768	Approved
0.6891	Remote Similarity	NPD4767	Approved
0.6881	Remote Similarity	NPD6684	Approved
0.6881	Remote Similarity	NPD7521	Approved
0.6881	Remote Similarity	NPD5330	Approved
0.6881	Remote Similarity	NPD7146	Approved
0.6881	Remote Similarity	NPD6409	Approved
0.6881	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD6079	Approved
0.687	Remote Similarity	NPD6033	Approved
0.687	Remote Similarity	NPD5173	Approved
0.686	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4753	Phase 2
0.6847	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5328	Approved
0.6847	Remote Similarity	NPD6101	Approved
0.6847	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD5210	Approved
0.6842	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6412	Phase 2
0.6803	Remote Similarity	NPD5248	Approved
0.6803	Remote Similarity	NPD5247	Approved
0.6803	Remote Similarity	NPD5251	Approved
0.6803	Remote Similarity	NPD5249	Phase 3
0.6803	Remote Similarity	NPD5250	Approved
0.6789	Remote Similarity	NPD1694	Approved
0.6786	Remote Similarity	NPD7838	Discovery
0.6777	Remote Similarity	NPD5128	Approved
0.6757	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6903	Approved
0.6727	Remote Similarity	NPD3618	Phase 1
0.6727	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6098	Approved
0.6726	Remote Similarity	NPD6050	Approved
0.6723	Remote Similarity	NPD4754	Approved
0.6697	Remote Similarity	NPD4786	Approved
0.6696	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7327	Approved
0.6693	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6641	Remote Similarity	NPD7516	Approved
0.664	Remote Similarity	NPD8133	Approved
0.6637	Remote Similarity	NPD5785	Approved
0.6637	Remote Similarity	NPD5692	Phase 3
0.6636	Remote Similarity	NPD5329	Approved
0.6613	Remote Similarity	NPD5215	Approved
0.6613	Remote Similarity	NPD5216	Approved
0.6613	Remote Similarity	NPD5217	Approved
0.6589	Remote Similarity	NPD8294	Approved
0.6589	Remote Similarity	NPD8377	Approved
0.6579	Remote Similarity	NPD7983	Approved
0.6579	Remote Similarity	NPD8035	Phase 2
0.6579	Remote Similarity	NPD5694	Approved
0.6579	Remote Similarity	NPD7637	Suspended
0.6579	Remote Similarity	NPD8034	Phase 2
0.6547	Remote Similarity	NPD6333	Approved
0.6547	Remote Similarity	NPD6334	Approved
0.6545	Remote Similarity	NPD3665	Phase 1
0.6545	Remote Similarity	NPD3133	Approved
0.6545	Remote Similarity	NPD4197	Approved
0.6545	Remote Similarity	NPD3666	Approved
0.6538	Remote Similarity	NPD8379	Approved
0.6538	Remote Similarity	NPD8378	Approved
0.6538	Remote Similarity	NPD8296	Approved
0.6538	Remote Similarity	NPD8380	Approved
0.6538	Remote Similarity	NPD8335	Approved
0.6532	Remote Similarity	NPD5169	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