NPASS Compound

Structure

NPC229204 OpenBabel07101718292D 22 24 0 0 1 0 0 0 0 0999 V2000 -3.5922 1.0484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8441 -0.1485 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 -0.7592 -1.3317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -0.8262 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4796 -2.0920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8727 0.0886 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 -2.1906 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3601 -1.6182 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 -3.1816 -0.6342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -1.4010 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 -4.2611 -2.0520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 18 2 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 1 0 0 0 15 20 1 6 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 20 1 6 0 0 0 17 22 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	3.75
LogD:	3.775
LogS:	-4.536
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	4.653
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.655
MDCK Permeability:	1.6341058653779328e-05
Pgp-inhibitor:	0.912
Pgp-substrate:	0.144
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.757
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.545
Plasma Protein Binding (PPB):	75.55958557128906%
Volume Distribution (VD):	0.692
Pgp-substrate:	17.279888153076172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.292
CYP2C19-inhibitor:	0.147
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.272
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.403

ADMET: Excretion

Clearance (CL):	8.313
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.161
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.715
Carcinogencity:	0.684
Eye Corrosion:	0.101
Eye Irritation:	0.504
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC229204

Natural Product ID:	NPC229204
*Common Name:**	(3Ar,4As,8R,8Ar,10As)-8-Hydroxy-1-Isopropylidene-3A,8A-Dimethyl-5-Methylene-Dodecahydro-Benzo[F]Azulen-2-One
IUPAC Name:	(3aS,5aR,6R,9aS,10aR)-6-hydroxy-5a,10a-dimethyl-9-methylidene-3-propan-2-ylidene-3a,4,5,6,7,8,9a,10-octahydro-1H-benzo[f]azulen-2-one
Synonyms:
Standard InCHIKey:	LMMZVHYQOQHVCE-DQIJQRSUSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-12(2)18-14-8-9-20(5)15(13(3)6-7-17(20)22)10-19(14,4)11-16(18)21/h14-15,17,22H,3,6-11H2,1-2,4-5H3/t14-,15+,17-,19-,20-/m1/s1
SMILES:	CC(=C1[C@H]2CC[C@]3(C)[C@@H](C[C@]2(C)CC1=O)C(=C)CC[C@H]3O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094088
PubChem CID:	46887664
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
NPO32701	Eunicea	Genus	Plexauridae	Eukaryota	n.a.	southwestern Caribbean	n.a.	PMID[20384296]

☑ 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
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	<=	50.0	%	PMID[512614]

☑ 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 NPC229204 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	147
0.1-0.2	1235
0.2-0.3	6099
0.3-0.4	15744
0.4-0.5	7392
0.5-0.6	6773
0.6-0.7	4474
0.7-0.8	783
0.8-0.85	46
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8974	High Similarity	NPC136150
0.8765	High Similarity	NPC470574
0.8701	High Similarity	NPC197659
0.8659	High Similarity	NPC72133
0.8554	High Similarity	NPC141292
0.8452	Intermediate Similarity	NPC292491
0.8452	Intermediate Similarity	NPC328539
0.8452	Intermediate Similarity	NPC310752
0.8452	Intermediate Similarity	NPC143767
0.8452	Intermediate Similarity	NPC131470
0.8452	Intermediate Similarity	NPC471722
0.8415	Intermediate Similarity	NPC58841
0.8415	Intermediate Similarity	NPC214043
0.8415	Intermediate Similarity	NPC473246
0.8415	Intermediate Similarity	NPC329043
0.8415	Intermediate Similarity	NPC321187
0.8415	Intermediate Similarity	NPC85774
0.8415	Intermediate Similarity	NPC161423
0.8415	Intermediate Similarity	NPC227064
0.8375	Intermediate Similarity	NPC172013
0.8353	Intermediate Similarity	NPC86319
0.8353	Intermediate Similarity	NPC275740
0.8333	Intermediate Similarity	NPC475740
0.8333	Intermediate Similarity	NPC469646
0.8313	Intermediate Similarity	NPC197823
0.8256	Intermediate Similarity	NPC126993
0.8256	Intermediate Similarity	NPC191684
0.8256	Intermediate Similarity	NPC183283
0.825	Intermediate Similarity	NPC308038
0.825	Intermediate Similarity	NPC281138
0.8235	Intermediate Similarity	NPC472802
0.8235	Intermediate Similarity	NPC471724
0.8214	Intermediate Similarity	NPC31564
0.8214	Intermediate Similarity	NPC327115
0.8214	Intermediate Similarity	NPC145879
0.8214	Intermediate Similarity	NPC474732
0.8214	Intermediate Similarity	NPC474778
0.8214	Intermediate Similarity	NPC474733
0.8205	Intermediate Similarity	NPC114236
0.8193	Intermediate Similarity	NPC237712
0.8171	Intermediate Similarity	NPC151519
0.8161	Intermediate Similarity	NPC155304
0.8161	Intermediate Similarity	NPC168027
0.8161	Intermediate Similarity	NPC272746
0.8161	Intermediate Similarity	NPC185936
0.8161	Intermediate Similarity	NPC63748
0.8161	Intermediate Similarity	NPC233116
0.8148	Intermediate Similarity	NPC45495
0.814	Intermediate Similarity	NPC473999
0.814	Intermediate Similarity	NPC119416
0.814	Intermediate Similarity	NPC309603
0.814	Intermediate Similarity	NPC1015
0.814	Intermediate Similarity	NPC31985
0.8125	Intermediate Similarity	NPC178852
0.8118	Intermediate Similarity	NPC58063
0.8118	Intermediate Similarity	NPC136548
0.8101	Intermediate Similarity	NPC263582
0.8101	Intermediate Similarity	NPC250621
0.8095	Intermediate Similarity	NPC79573
0.8095	Intermediate Similarity	NPC469948
0.8072	Intermediate Similarity	NPC278648
0.8072	Intermediate Similarity	NPC470165
0.8072	Intermediate Similarity	NPC64600
0.8072	Intermediate Similarity	NPC476082
0.8068	Intermediate Similarity	NPC69454
0.8068	Intermediate Similarity	NPC475255
0.8068	Intermediate Similarity	NPC12722
0.8046	Intermediate Similarity	NPC85173
0.8046	Intermediate Similarity	NPC48010
0.8025	Intermediate Similarity	NPC7232
0.8025	Intermediate Similarity	NPC181195
0.8025	Intermediate Similarity	NPC472490
0.8025	Intermediate Similarity	NPC261125
0.8023	Intermediate Similarity	NPC474677
0.8023	Intermediate Similarity	NPC193360
0.8	Intermediate Similarity	NPC118648
0.8	Intermediate Similarity	NPC94755
0.8	Intermediate Similarity	NPC158393
0.8	Intermediate Similarity	NPC471737
0.8	Intermediate Similarity	NPC55309
0.8	Intermediate Similarity	NPC472985
0.8	Intermediate Similarity	NPC475022
0.8	Intermediate Similarity	NPC222613
0.8	Intermediate Similarity	NPC28252
0.8	Intermediate Similarity	NPC472986
0.7978	Intermediate Similarity	NPC196485
0.7978	Intermediate Similarity	NPC111015
0.7978	Intermediate Similarity	NPC474690
0.7978	Intermediate Similarity	NPC299100
0.7978	Intermediate Similarity	NPC245972
0.7978	Intermediate Similarity	NPC166906
0.7976	Intermediate Similarity	NPC221758
0.7976	Intermediate Similarity	NPC59453
0.7976	Intermediate Similarity	NPC82902
0.7975	Intermediate Similarity	NPC474011
0.7973	Intermediate Similarity	NPC474329
0.7973	Intermediate Similarity	NPC474304
0.7955	Intermediate Similarity	NPC475806
0.7955	Intermediate Similarity	NPC473998
0.7952	Intermediate Similarity	NPC93590
0.7952	Intermediate Similarity	NPC48362
0.7931	Intermediate Similarity	NPC250592
0.7931	Intermediate Similarity	NPC77263
0.7931	Intermediate Similarity	NPC186688
0.7931	Intermediate Similarity	NPC26959
0.7931	Intermediate Similarity	NPC477943
0.7931	Intermediate Similarity	NPC214387
0.7931	Intermediate Similarity	NPC268406
0.7927	Intermediate Similarity	NPC164999
0.7927	Intermediate Similarity	NPC148685
0.7927	Intermediate Similarity	NPC2482
0.7927	Intermediate Similarity	NPC104120
0.7927	Intermediate Similarity	NPC472478
0.7927	Intermediate Similarity	NPC157895
0.7922	Intermediate Similarity	NPC280256
0.7907	Intermediate Similarity	NPC142361
0.7907	Intermediate Similarity	NPC187376
0.7907	Intermediate Similarity	NPC233836
0.7907	Intermediate Similarity	NPC159046
0.7907	Intermediate Similarity	NPC93778
0.7907	Intermediate Similarity	NPC287079
0.7907	Intermediate Similarity	NPC474684
0.7901	Intermediate Similarity	NPC297996
0.7901	Intermediate Similarity	NPC62336
0.7901	Intermediate Similarity	NPC475994
0.7889	Intermediate Similarity	NPC180950
0.7889	Intermediate Similarity	NPC470016
0.7889	Intermediate Similarity	NPC259286
0.7889	Intermediate Similarity	NPC88310
0.7889	Intermediate Similarity	NPC317586
0.7889	Intermediate Similarity	NPC271195
0.7882	Intermediate Similarity	NPC202868
0.7882	Intermediate Similarity	NPC471224
0.7882	Intermediate Similarity	NPC76518
0.7882	Intermediate Similarity	NPC474083
0.7882	Intermediate Similarity	NPC474218
0.7875	Intermediate Similarity	NPC1973
0.7875	Intermediate Similarity	NPC470525
0.7875	Intermediate Similarity	NPC167873
0.7875	Intermediate Similarity	NPC215481
0.7865	Intermediate Similarity	NPC472930
0.7865	Intermediate Similarity	NPC134826
0.7865	Intermediate Similarity	NPC109305
0.7857	Intermediate Similarity	NPC475726
0.7857	Intermediate Similarity	NPC471036
0.7857	Intermediate Similarity	NPC472743
0.7857	Intermediate Similarity	NPC291320
0.7857	Intermediate Similarity	NPC118800
0.7848	Intermediate Similarity	NPC78527
0.7848	Intermediate Similarity	NPC102313
0.7848	Intermediate Similarity	NPC199316
0.7848	Intermediate Similarity	NPC469691
0.7848	Intermediate Similarity	NPC470299
0.7848	Intermediate Similarity	NPC167049
0.7841	Intermediate Similarity	NPC477149
0.7841	Intermediate Similarity	NPC477147
0.7831	Intermediate Similarity	NPC121984
0.7831	Intermediate Similarity	NPC101012
0.7831	Intermediate Similarity	NPC473420
0.7831	Intermediate Similarity	NPC477372
0.7816	Intermediate Similarity	NPC158778
0.7816	Intermediate Similarity	NPC242864
0.7802	Intermediate Similarity	NPC249954
0.7802	Intermediate Similarity	NPC328162
0.7802	Intermediate Similarity	NPC471153
0.7802	Intermediate Similarity	NPC301534
0.7802	Intermediate Similarity	NPC250757
0.7802	Intermediate Similarity	NPC96859
0.7802	Intermediate Similarity	NPC305483
0.7802	Intermediate Similarity	NPC192428
0.7792	Intermediate Similarity	NPC475952
0.7791	Intermediate Similarity	NPC20688
0.7791	Intermediate Similarity	NPC194417
0.7791	Intermediate Similarity	NPC179591
0.7791	Intermediate Similarity	NPC476043
0.7791	Intermediate Similarity	NPC51014
0.7791	Intermediate Similarity	NPC472974
0.7791	Intermediate Similarity	NPC469994
0.7778	Intermediate Similarity	NPC74995
0.7778	Intermediate Similarity	NPC106078
0.7778	Intermediate Similarity	NPC470428
0.7778	Intermediate Similarity	NPC8993
0.7778	Intermediate Similarity	NPC276769
0.7765	Intermediate Similarity	NPC475745
0.7765	Intermediate Similarity	NPC165064
0.7765	Intermediate Similarity	NPC146683
0.7765	Intermediate Similarity	NPC470812
0.7765	Intermediate Similarity	NPC474482
0.7765	Intermediate Similarity	NPC472265
0.7763	Intermediate Similarity	NPC263161
0.7753	Intermediate Similarity	NPC19114
0.7753	Intermediate Similarity	NPC131872
0.7742	Intermediate Similarity	NPC112167
0.7738	Intermediate Similarity	NPC103486
0.7738	Intermediate Similarity	NPC110780
0.7738	Intermediate Similarity	NPC193347
0.7727	Intermediate Similarity	NPC472971
0.7727	Intermediate Similarity	NPC77168
0.7727	Intermediate Similarity	NPC123912
0.7727	Intermediate Similarity	NPC229871

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 NPC229204 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1718
0.2-0.3	4279
0.3-0.4	2133
0.4-0.5	454
0.5-0.6	164
0.6-0.7	208
0.7-0.8	49
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8659	High Similarity	NPD3618	Phase 1
0.8415	Intermediate Similarity	NPD3133	Approved
0.8415	Intermediate Similarity	NPD3665	Phase 1
0.8415	Intermediate Similarity	NPD3666	Approved
0.8353	Intermediate Similarity	NPD5328	Approved
0.8214	Intermediate Similarity	NPD5279	Phase 3
0.8171	Intermediate Similarity	NPD3667	Approved
0.8161	Intermediate Similarity	NPD6079	Approved
0.8068	Intermediate Similarity	NPD4202	Approved
0.7976	Intermediate Similarity	NPD4786	Approved
0.7802	Intermediate Similarity	NPD5221	Approved
0.7802	Intermediate Similarity	NPD5222	Approved
0.7802	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD4697	Phase 3
0.7738	Intermediate Similarity	NPD4223	Phase 3
0.7738	Intermediate Similarity	NPD4221	Approved
0.7727	Intermediate Similarity	NPD4753	Phase 2
0.7717	Intermediate Similarity	NPD4755	Approved
0.7717	Intermediate Similarity	NPD5173	Approved
0.7683	Intermediate Similarity	NPD3617	Approved
0.7586	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4197	Approved
0.7556	Intermediate Similarity	NPD7515	Phase 2
0.7553	Intermediate Similarity	NPD5286	Approved
0.7553	Intermediate Similarity	NPD4700	Approved
0.7553	Intermediate Similarity	NPD5285	Approved
0.7553	Intermediate Similarity	NPD4696	Approved
0.7474	Intermediate Similarity	NPD5223	Approved
0.7471	Intermediate Similarity	NPD5329	Approved
0.7471	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4788	Approved
0.7396	Intermediate Similarity	NPD4633	Approved
0.7396	Intermediate Similarity	NPD5211	Phase 2
0.7396	Intermediate Similarity	NPD5225	Approved
0.7396	Intermediate Similarity	NPD5226	Approved
0.7396	Intermediate Similarity	NPD5224	Approved
0.7386	Intermediate Similarity	NPD4688	Approved
0.7386	Intermediate Similarity	NPD4694	Approved
0.7386	Intermediate Similarity	NPD4690	Approved
0.7386	Intermediate Similarity	NPD4138	Approved
0.7386	Intermediate Similarity	NPD4689	Approved
0.7386	Intermediate Similarity	NPD4693	Phase 3
0.7386	Intermediate Similarity	NPD6409	Approved
0.7386	Intermediate Similarity	NPD5205	Approved
0.7386	Intermediate Similarity	NPD6684	Approved
0.7386	Intermediate Similarity	NPD7334	Approved
0.7386	Intermediate Similarity	NPD7521	Approved
0.7386	Intermediate Similarity	NPD5690	Phase 2
0.7386	Intermediate Similarity	NPD7146	Approved
0.7386	Intermediate Similarity	NPD5280	Approved
0.7386	Intermediate Similarity	NPD5330	Approved
0.7356	Intermediate Similarity	NPD3668	Phase 3
0.732	Intermediate Similarity	NPD5175	Approved
0.732	Intermediate Similarity	NPD5174	Approved
0.732	Intermediate Similarity	NPD4754	Approved
0.7312	Intermediate Similarity	NPD4629	Approved
0.7312	Intermediate Similarity	NPD5210	Approved
0.7294	Intermediate Similarity	NPD4695	Discontinued
0.7262	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5141	Approved
0.7222	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6903	Approved
0.7204	Intermediate Similarity	NPD7748	Approved
0.7195	Intermediate Similarity	NPD6924	Approved
0.7195	Intermediate Similarity	NPD6926	Approved
0.7172	Intermediate Similarity	NPD6675	Approved
0.7172	Intermediate Similarity	NPD6402	Approved
0.7172	Intermediate Similarity	NPD7128	Approved
0.7172	Intermediate Similarity	NPD4767	Approved
0.7172	Intermediate Similarity	NPD4768	Approved
0.7172	Intermediate Similarity	NPD5739	Approved
0.7158	Intermediate Similarity	NPD6083	Phase 2
0.7158	Intermediate Similarity	NPD6084	Phase 2
0.7128	Intermediate Similarity	NPD5695	Phase 3
0.7125	Intermediate Similarity	NPD4137	Phase 3
0.7125	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5701	Approved
0.71	Intermediate Similarity	NPD5697	Approved
0.7097	Intermediate Similarity	NPD6399	Phase 3
0.7093	Intermediate Similarity	NPD7525	Registered
0.7083	Intermediate Similarity	NPD7638	Approved
0.7065	Intermediate Similarity	NPD4096	Approved
0.7051	Intermediate Similarity	NPD7341	Phase 2
0.7051	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4691	Approved
0.7037	Intermediate Similarity	NPD4747	Approved
0.7033	Intermediate Similarity	NPD6672	Approved
0.7033	Intermediate Similarity	NPD5737	Approved
0.7033	Intermediate Similarity	NPD4518	Approved
0.703	Intermediate Similarity	NPD5128	Approved
0.703	Intermediate Similarity	NPD4730	Approved
0.703	Intermediate Similarity	NPD6899	Approved
0.703	Intermediate Similarity	NPD6011	Approved
0.703	Intermediate Similarity	NPD6881	Approved
0.703	Intermediate Similarity	NPD4729	Approved
0.703	Intermediate Similarity	NPD5168	Approved
0.703	Intermediate Similarity	NPD7320	Approved
0.7024	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6933	Approved
0.7011	Intermediate Similarity	NPD4692	Approved
0.7011	Intermediate Similarity	NPD4139	Approved
0.701	Intermediate Similarity	NPD7639	Approved
0.701	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD4519	Discontinued
0.7	Intermediate Similarity	NPD4623	Approved
0.6989	Remote Similarity	NPD5284	Approved
0.6989	Remote Similarity	NPD5281	Approved
0.6979	Remote Similarity	NPD7902	Approved
0.6977	Remote Similarity	NPD4195	Approved
0.6962	Remote Similarity	NPD7331	Phase 2
0.6961	Remote Similarity	NPD6372	Approved
0.6961	Remote Similarity	NPD6014	Approved
0.6961	Remote Similarity	NPD6012	Approved
0.6961	Remote Similarity	NPD6373	Approved
0.6961	Remote Similarity	NPD6013	Approved
0.6951	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5276	Approved
0.6951	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3698	Phase 2
0.6914	Remote Similarity	NPD6923	Approved
0.6914	Remote Similarity	NPD6922	Approved
0.6907	Remote Similarity	NPD5696	Approved
0.6905	Remote Similarity	NPD3703	Phase 2
0.6905	Remote Similarity	NPD6942	Approved
0.6905	Remote Similarity	NPD7339	Approved
0.6897	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5368	Approved
0.6893	Remote Similarity	NPD6883	Approved
0.6893	Remote Similarity	NPD5251	Approved
0.6893	Remote Similarity	NPD7102	Approved
0.6893	Remote Similarity	NPD4634	Approved
0.6893	Remote Similarity	NPD5249	Phase 3
0.6893	Remote Similarity	NPD7290	Approved
0.6893	Remote Similarity	NPD5169	Approved
0.6893	Remote Similarity	NPD5248	Approved
0.6893	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5250	Approved
0.6893	Remote Similarity	NPD5247	Approved
0.6893	Remote Similarity	NPD5135	Approved
0.6889	Remote Similarity	NPD1694	Approved
0.6889	Remote Similarity	NPD5363	Approved
0.6882	Remote Similarity	NPD5785	Approved
0.6829	Remote Similarity	NPD4245	Approved
0.6829	Remote Similarity	NPD7143	Approved
0.6829	Remote Similarity	NPD7144	Approved
0.6829	Remote Similarity	NPD4244	Approved
0.6827	Remote Similarity	NPD8130	Phase 1
0.6827	Remote Similarity	NPD5127	Approved
0.6827	Remote Similarity	NPD5215	Approved
0.6827	Remote Similarity	NPD6617	Approved
0.6827	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5216	Approved
0.6827	Remote Similarity	NPD6869	Approved
0.6827	Remote Similarity	NPD6650	Approved
0.6827	Remote Similarity	NPD5217	Approved
0.6827	Remote Similarity	NPD6649	Approved
0.6827	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD5369	Approved
0.6809	Remote Similarity	NPD8034	Phase 2
0.6809	Remote Similarity	NPD8035	Phase 2
0.6786	Remote Similarity	NPD5733	Approved
0.6786	Remote Similarity	NPD4687	Approved
0.6786	Remote Similarity	NPD4058	Approved
0.6782	Remote Similarity	NPD6929	Approved
0.6771	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6412	Phase 2
0.6762	Remote Similarity	NPD8297	Approved
0.6762	Remote Similarity	NPD6882	Approved
0.6747	Remote Similarity	NPD7152	Approved
0.6747	Remote Similarity	NPD7151	Approved
0.6747	Remote Similarity	NPD7150	Approved
0.6742	Remote Similarity	NPD4270	Approved
0.6742	Remote Similarity	NPD4269	Approved
0.6742	Remote Similarity	NPD6435	Approved
0.6742	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5133	Approved
0.6735	Remote Similarity	NPD5290	Discontinued
0.6705	Remote Similarity	NPD7509	Discontinued
0.6705	Remote Similarity	NPD6930	Phase 2
0.6705	Remote Similarity	NPD6931	Approved
0.6698	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6636	Remote Similarity	NPD5167	Approved
0.6632	Remote Similarity	NPD6411	Approved
0.6628	Remote Similarity	NPD6117	Approved
0.6627	Remote Similarity	NPD4789	Approved
0.6596	Remote Similarity	NPD6080	Approved
0.6596	Remote Similarity	NPD6904	Approved
0.6596	Remote Similarity	NPD6673	Approved
0.6591	Remote Similarity	NPD7645	Phase 2
0.6588	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6868	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