NPASS Compound

Structure

CID210323 OpenBabel06191716002D 22 24 0 0 1 0 0 0 0 0999 V2000 -4.6888 -4.2247 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 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2575 -2.3912 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 -3.7229 -3.9659 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 -1.7321 0.0000 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 -3.5000 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 -2.5981 -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 -0.8660 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 1 0 0 0 15 19 1 1 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 1 0 0 0 18 4 1 1 0 0 0 19 5 1 1 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.26
Volume:	343.751
LogP:	3.726
LogD:	3.515
LogS:	-4.011
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	4.552
Fsp3:	0.9
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:	-4.765
MDCK Permeability:	2.0973573555238545e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.247
30% Bioavailability (F30%):	0.217

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	86.22589874267578%
Volume Distribution (VD):	1.098
Pgp-substrate:	18.195537567138672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.481
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.093
CYP2C9-substrate:	0.252
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	6.914
Half-life (T1/2):	0.268

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.243
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.652
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.576
Carcinogencity:	0.029
Eye Corrosion:	0.896
Eye Irritation:	0.262
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC210323

Natural Product ID:	NPC210323
*Common Name:**	15-Isopimaren-3Beta,8Beta-Diol
IUPAC Name:	(2S,4aS,4bR,7S,8aR,10aR)-7-ethenyl-1,1,4a,7-tetramethyl-2,3,4,4b,5,6,8,9,10,10a-decahydrophenanthrene-2,8a-diol
Synonyms:
Standard InCHIKey:	UIVFXGICZLHPQO-CJEFFJQMSA-N
Standard InCHI:	InChI=1S/C20H34O2/c1-6-18(4)10-7-15-19(5)11-9-16(21)17(2,3)14(19)8-12-20(15,22)13-18/h6,14-16,21-22H,1,7-13H2,2-5H3/t14-,15+,16-,18-,19-,20+/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@@H]2[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@]2(C1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465546
PubChem CID:	21578007
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
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	Leaves and branches	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	leaves	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28256	Platycladus orientalis	Species	Cupressaceae	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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	80900.0	nM	PMID[571078]

☑ 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 NPC210323 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	195
0.1-0.2	2212
0.2-0.3	10087
0.3-0.4	15377
0.4-0.5	5805
0.5-0.6	5422
0.6-0.7	2591
0.7-0.8	835
0.8-0.85	150
0.85-0.9	19
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9844	High Similarity	NPC2648
0.8841	High Similarity	NPC167706
0.8824	High Similarity	NPC9942
0.875	High Similarity	NPC169994
0.875	High Similarity	NPC472746
0.875	High Similarity	NPC470758
0.875	High Similarity	NPC470711
0.8732	High Similarity	NPC3403
0.8732	High Similarity	NPC103822
0.8714	High Similarity	NPC182717
0.8714	High Similarity	NPC211009
0.8696	High Similarity	NPC45296
0.8636	High Similarity	NPC101128
0.863	High Similarity	NPC11908
0.863	High Similarity	NPC148977
0.863	High Similarity	NPC285761
0.8611	High Similarity	NPC470749
0.8611	High Similarity	NPC106432
0.8611	High Similarity	NPC63958
0.8611	High Similarity	NPC91573
0.8592	High Similarity	NPC100334
0.8592	High Similarity	NPC308440
0.8592	High Similarity	NPC477138
0.8592	High Similarity	NPC91858
0.8592	High Similarity	NPC243342
0.8592	High Similarity	NPC472503
0.8571	High Similarity	NPC301226
0.8571	High Similarity	NPC111234
0.8571	High Similarity	NPC110799
0.8529	High Similarity	NPC185874
0.8529	High Similarity	NPC253303
0.8529	High Similarity	NPC88454
0.8529	High Similarity	NPC101307
0.8529	High Similarity	NPC269077
0.8529	High Similarity	NPC139207
0.8529	High Similarity	NPC117607
0.8514	High Similarity	NPC80530
0.8514	High Similarity	NPC291379
0.8514	High Similarity	NPC273410
0.8507	High Similarity	NPC64123
0.8493	Intermediate Similarity	NPC471798
0.8493	Intermediate Similarity	NPC472805
0.8493	Intermediate Similarity	NPC101475
0.8493	Intermediate Similarity	NPC40394
0.8493	Intermediate Similarity	NPC34177
0.8493	Intermediate Similarity	NPC157996
0.8493	Intermediate Similarity	NPC90979
0.8472	Intermediate Similarity	NPC230704
0.8472	Intermediate Similarity	NPC185536
0.8472	Intermediate Similarity	NPC240235
0.8472	Intermediate Similarity	NPC34700
0.8472	Intermediate Similarity	NPC291503
0.8472	Intermediate Similarity	NPC212879
0.8472	Intermediate Similarity	NPC70982
0.8472	Intermediate Similarity	NPC231256
0.8472	Intermediate Similarity	NPC178383
0.8472	Intermediate Similarity	NPC144075
0.8472	Intermediate Similarity	NPC104387
0.8472	Intermediate Similarity	NPC138374
0.8451	Intermediate Similarity	NPC471799
0.8421	Intermediate Similarity	NPC296701
0.8421	Intermediate Similarity	NPC218616
0.8406	Intermediate Similarity	NPC94192
0.8406	Intermediate Similarity	NPC244790
0.84	Intermediate Similarity	NPC236237
0.84	Intermediate Similarity	NPC102253
0.84	Intermediate Similarity	NPC322313
0.84	Intermediate Similarity	NPC13554
0.8382	Intermediate Similarity	NPC476406
0.8378	Intermediate Similarity	NPC42853
0.8378	Intermediate Similarity	NPC472501
0.8378	Intermediate Similarity	NPC22955
0.8378	Intermediate Similarity	NPC99168
0.8378	Intermediate Similarity	NPC244385
0.8378	Intermediate Similarity	NPC31828
0.8378	Intermediate Similarity	NPC138621
0.8378	Intermediate Similarity	NPC167037
0.8378	Intermediate Similarity	NPC6978
0.8378	Intermediate Similarity	NPC301707
0.8378	Intermediate Similarity	NPC253807
0.8378	Intermediate Similarity	NPC137587
0.8378	Intermediate Similarity	NPC98386
0.8378	Intermediate Similarity	NPC72507
0.8378	Intermediate Similarity	NPC230295
0.8378	Intermediate Similarity	NPC474989
0.8378	Intermediate Similarity	NPC300499
0.8378	Intermediate Similarity	NPC470396
0.8378	Intermediate Similarity	NPC196753
0.8378	Intermediate Similarity	NPC158662
0.8378	Intermediate Similarity	NPC472342
0.8358	Intermediate Similarity	NPC144650
0.8356	Intermediate Similarity	NPC470766
0.8356	Intermediate Similarity	NPC78067
0.8356	Intermediate Similarity	NPC237460
0.8356	Intermediate Similarity	NPC30590
0.8356	Intermediate Similarity	NPC265588
0.8356	Intermediate Similarity	NPC120098
0.8356	Intermediate Similarity	NPC86305
0.8356	Intermediate Similarity	NPC290598
0.8356	Intermediate Similarity	NPC27765
0.8356	Intermediate Similarity	NPC122418
0.8356	Intermediate Similarity	NPC14112
0.8356	Intermediate Similarity	NPC278091
0.8356	Intermediate Similarity	NPC93662
0.8356	Intermediate Similarity	NPC265328
0.8333	Intermediate Similarity	NPC25511
0.8333	Intermediate Similarity	NPC201048
0.8333	Intermediate Similarity	NPC49168
0.8333	Intermediate Similarity	NPC476366
0.8333	Intermediate Similarity	NPC62657
0.8333	Intermediate Similarity	NPC196358
0.8333	Intermediate Similarity	NPC145552
0.8333	Intermediate Similarity	NPC254509
0.8333	Intermediate Similarity	NPC5046
0.8333	Intermediate Similarity	NPC162164
0.8333	Intermediate Similarity	NPC192638
0.8333	Intermediate Similarity	NPC471797
0.8333	Intermediate Similarity	NPC476736
0.8312	Intermediate Similarity	NPC134481
0.8312	Intermediate Similarity	NPC470558
0.8312	Intermediate Similarity	NPC82623
0.831	Intermediate Similarity	NPC242001
0.8281	Intermediate Similarity	NPC135438
0.8267	Intermediate Similarity	NPC49627
0.8267	Intermediate Similarity	NPC49599
0.8267	Intermediate Similarity	NPC472463
0.8267	Intermediate Similarity	NPC53744
0.8243	Intermediate Similarity	NPC307336
0.8243	Intermediate Similarity	NPC212241
0.8243	Intermediate Similarity	NPC331618
0.8243	Intermediate Similarity	NPC260301
0.8243	Intermediate Similarity	NPC138502
0.8243	Intermediate Similarity	NPC119355
0.8243	Intermediate Similarity	NPC91594
0.8243	Intermediate Similarity	NPC248830
0.8243	Intermediate Similarity	NPC257191
0.8243	Intermediate Similarity	NPC202540
0.8235	Intermediate Similarity	NPC172613
0.8235	Intermediate Similarity	NPC11555
0.8235	Intermediate Similarity	NPC208198
0.8235	Intermediate Similarity	NPC260116
0.8235	Intermediate Similarity	NPC282619
0.8235	Intermediate Similarity	NPC80463
0.8235	Intermediate Similarity	NPC60837
0.8235	Intermediate Similarity	NPC258595
0.8235	Intermediate Similarity	NPC2728
0.8219	Intermediate Similarity	NPC66566
0.8219	Intermediate Similarity	NPC200243
0.8219	Intermediate Similarity	NPC477923
0.8205	Intermediate Similarity	NPC474493
0.8194	Intermediate Similarity	NPC195489
0.8194	Intermediate Similarity	NPC68443
0.8169	Intermediate Similarity	NPC145498
0.8158	Intermediate Similarity	NPC295131
0.8143	Intermediate Similarity	NPC245795
0.8143	Intermediate Similarity	NPC276616
0.8133	Intermediate Similarity	NPC312328
0.8133	Intermediate Similarity	NPC65897
0.8133	Intermediate Similarity	NPC472500
0.8133	Intermediate Similarity	NPC302041
0.8133	Intermediate Similarity	NPC477819
0.8133	Intermediate Similarity	NPC472499
0.8133	Intermediate Similarity	NPC477817
0.8133	Intermediate Similarity	NPC85346
0.8133	Intermediate Similarity	NPC102708
0.8116	Intermediate Similarity	NPC473929
0.8108	Intermediate Similarity	NPC129165
0.8108	Intermediate Similarity	NPC106364
0.8108	Intermediate Similarity	NPC189883
0.8108	Intermediate Similarity	NPC104806
0.8108	Intermediate Similarity	NPC134330
0.8108	Intermediate Similarity	NPC38141
0.8101	Intermediate Similarity	NPC164424
0.8101	Intermediate Similarity	NPC477578
0.8088	Intermediate Similarity	NPC68656
0.8082	Intermediate Similarity	NPC38426
0.8077	Intermediate Similarity	NPC193870
0.8077	Intermediate Similarity	NPC141941
0.8077	Intermediate Similarity	NPC207013
0.8077	Intermediate Similarity	NPC82538
0.8077	Intermediate Similarity	NPC477818
0.8077	Intermediate Similarity	NPC237795
0.8056	Intermediate Similarity	NPC164022
0.8052	Intermediate Similarity	NPC116202
0.8052	Intermediate Similarity	NPC249423
0.8052	Intermediate Similarity	NPC476646
0.8052	Intermediate Similarity	NPC242350
0.8028	Intermediate Similarity	NPC476431
0.8026	Intermediate Similarity	NPC1319
0.8026	Intermediate Similarity	NPC476367
0.8026	Intermediate Similarity	NPC472742
0.8026	Intermediate Similarity	NPC475727
0.8026	Intermediate Similarity	NPC80297
0.8026	Intermediate Similarity	NPC24504
0.8026	Intermediate Similarity	NPC476316
0.8026	Intermediate Similarity	NPC72755
0.8026	Intermediate Similarity	NPC116119
0.8	Intermediate Similarity	NPC477924
0.8	Intermediate Similarity	NPC155986
0.8	Intermediate Similarity	NPC198968

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 NPC210323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	2640
0.2-0.3	4055
0.3-0.4	1629
0.4-0.5	316
0.5-0.6	199
0.6-0.7	121
0.7-0.8	14
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD7525	Registered
0.8267	Intermediate Similarity	NPD7645	Phase 2
0.7778	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6942	Approved
0.7733	Intermediate Similarity	NPD7339	Approved
0.7632	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4787	Phase 1
0.7368	Intermediate Similarity	NPD6926	Approved
0.7368	Intermediate Similarity	NPD6924	Approved
0.7179	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD4784	Approved
0.7143	Intermediate Similarity	NPD4785	Approved
0.7126	Intermediate Similarity	NPD6079	Approved
0.7126	Intermediate Similarity	NPD7515	Phase 2
0.7108	Intermediate Similarity	NPD4786	Approved
0.7105	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4243	Approved
0.7105	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7150	Approved
0.7105	Intermediate Similarity	NPD7152	Approved
0.7105	Intermediate Similarity	NPD7151	Approved
0.7093	Intermediate Similarity	NPD5328	Approved
0.7073	Intermediate Similarity	NPD3667	Approved
0.7067	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD8264	Approved
0.7037	Intermediate Similarity	NPD4748	Discontinued
0.7037	Intermediate Similarity	NPD7509	Discontinued
0.6988	Remote Similarity	NPD4788	Approved
0.6974	Remote Similarity	NPD7144	Approved
0.6974	Remote Similarity	NPD7143	Approved
0.6962	Remote Similarity	NPD6117	Approved
0.6923	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6932	Approved
0.6875	Remote Similarity	NPD6116	Phase 1
0.686	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4202	Approved
0.6842	Remote Similarity	NPD6923	Approved
0.6842	Remote Similarity	NPD6922	Approved
0.6835	Remote Similarity	NPD3703	Phase 2
0.6829	Remote Similarity	NPD6930	Phase 2
0.6829	Remote Similarity	NPD6931	Approved
0.679	Remote Similarity	NPD6697	Approved
0.679	Remote Similarity	NPD6114	Approved
0.679	Remote Similarity	NPD6118	Approved
0.679	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6115	Approved
0.6778	Remote Similarity	NPD7748	Approved
0.6753	Remote Similarity	NPD4245	Approved
0.6753	Remote Similarity	NPD4244	Approved
0.6742	Remote Similarity	NPD8034	Phase 2
0.6742	Remote Similarity	NPD8035	Phase 2
0.6719	Remote Similarity	NPD385	Approved
0.6719	Remote Similarity	NPD384	Approved
0.6711	Remote Similarity	NPD5360	Phase 3
0.6711	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4195	Approved
0.6707	Remote Similarity	NPD6929	Approved
0.6706	Remote Similarity	NPD3666	Approved
0.6706	Remote Similarity	NPD3665	Phase 1
0.6706	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.663	Remote Similarity	NPD5222	Approved
0.663	Remote Similarity	NPD5221	Approved
0.663	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7332	Phase 2
0.6627	Remote Similarity	NPD7514	Phase 3
0.6625	Remote Similarity	NPD5275	Approved
0.6625	Remote Similarity	NPD4190	Phase 3
0.6623	Remote Similarity	NPD3698	Phase 2
0.6596	Remote Similarity	NPD5285	Approved
0.6596	Remote Similarity	NPD7639	Approved
0.6596	Remote Similarity	NPD5286	Approved
0.6596	Remote Similarity	NPD4696	Approved
0.6596	Remote Similarity	NPD7640	Approved
0.6588	Remote Similarity	NPD6695	Phase 3
0.6585	Remote Similarity	NPD7145	Approved
0.6559	Remote Similarity	NPD5173	Approved
0.6559	Remote Similarity	NPD4755	Approved
0.6559	Remote Similarity	NPD7902	Approved
0.6538	Remote Similarity	NPD4789	Approved
0.6526	Remote Similarity	NPD5223	Approved
0.6512	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD6683	Phase 2
0.6489	Remote Similarity	NPD5290	Discontinued
0.6463	Remote Similarity	NPD6925	Approved
0.6463	Remote Similarity	NPD5776	Phase 2
0.6458	Remote Similarity	NPD5225	Approved
0.6458	Remote Similarity	NPD5211	Phase 2
0.6458	Remote Similarity	NPD5226	Approved
0.6458	Remote Similarity	NPD4633	Approved
0.6458	Remote Similarity	NPD5224	Approved
0.6452	Remote Similarity	NPD4697	Phase 3
0.6437	Remote Similarity	NPD6893	Approved
0.6429	Remote Similarity	NPD6928	Phase 2
0.6421	Remote Similarity	NPD4700	Approved
0.6392	Remote Similarity	NPD5175	Approved
0.6392	Remote Similarity	NPD5174	Approved
0.6386	Remote Similarity	NPD3671	Phase 1
0.6364	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6902	Approved
0.6353	Remote Similarity	NPD6898	Phase 1
0.6351	Remote Similarity	NPD368	Approved
0.6333	Remote Similarity	NPD4753	Phase 2
0.6327	Remote Similarity	NPD5141	Approved
0.6322	Remote Similarity	NPD3668	Phase 3
0.6316	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6399	Phase 3
0.63	Remote Similarity	NPD6881	Approved
0.63	Remote Similarity	NPD6899	Approved
0.63	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7524	Approved
0.6292	Remote Similarity	NPD7750	Discontinued
0.6279	Remote Similarity	NPD4223	Phase 3
0.6279	Remote Similarity	NPD4221	Approved
0.6263	Remote Similarity	NPD5739	Approved
0.6263	Remote Similarity	NPD6402	Approved
0.6263	Remote Similarity	NPD6675	Approved
0.6263	Remote Similarity	NPD7128	Approved
0.625	Remote Similarity	NPD4758	Discontinued
0.625	Remote Similarity	NPD5329	Approved
0.6237	Remote Similarity	NPD7900	Approved
0.6237	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4754	Approved
0.62	Remote Similarity	NPD5697	Approved
0.6184	Remote Similarity	NPD371	Approved
0.618	Remote Similarity	NPD5279	Phase 3
0.618	Remote Similarity	NPD4519	Discontinued
0.618	Remote Similarity	NPD4623	Approved
0.6176	Remote Similarity	NPD7290	Approved
0.6176	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD6883	Approved
0.617	Remote Similarity	NPD4629	Approved
0.617	Remote Similarity	NPD5210	Approved
0.6139	Remote Similarity	NPD6011	Approved
0.6139	Remote Similarity	NPD4729	Approved
0.6139	Remote Similarity	NPD4730	Approved
0.6139	Remote Similarity	NPD7320	Approved
0.6136	Remote Similarity	NPD4197	Approved
0.6122	Remote Similarity	NPD7632	Discontinued
0.6117	Remote Similarity	NPD6847	Approved
0.6117	Remote Similarity	NPD6869	Approved
0.6117	Remote Similarity	NPD6649	Approved
0.6117	Remote Similarity	NPD6617	Approved
0.6117	Remote Similarity	NPD6650	Approved
0.6117	Remote Similarity	NPD8130	Phase 1
0.6111	Remote Similarity	NPD3573	Approved
0.61	Remote Similarity	NPD4768	Approved
0.61	Remote Similarity	NPD4767	Approved
0.6078	Remote Similarity	NPD6013	Approved
0.6078	Remote Similarity	NPD6373	Approved
0.6078	Remote Similarity	NPD6014	Approved
0.6078	Remote Similarity	NPD6012	Approved
0.6078	Remote Similarity	NPD6372	Approved
0.6076	Remote Similarity	NPD6705	Phase 1
0.6061	Remote Similarity	NPD388	Approved
0.6061	Remote Similarity	NPD386	Approved
0.6058	Remote Similarity	NPD6882	Approved
0.6058	Remote Similarity	NPD8297	Approved
0.6047	Remote Similarity	NPD4695	Discontinued
0.6044	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6083	Phase 2
0.6042	Remote Similarity	NPD6084	Phase 2
0.604	Remote Similarity	NPD5701	Approved
0.6026	Remote Similarity	NPD4224	Phase 2
0.6022	Remote Similarity	NPD7087	Discontinued
0.6022	Remote Similarity	NPD6411	Approved
0.602	Remote Similarity	NPD4159	Approved
0.6019	Remote Similarity	NPD5251	Approved
0.6019	Remote Similarity	NPD5250	Approved
0.6019	Remote Similarity	NPD5135	Approved
0.6019	Remote Similarity	NPD5169	Approved
0.6019	Remote Similarity	NPD5249	Phase 3
0.6019	Remote Similarity	NPD5248	Approved
0.6019	Remote Similarity	NPD5247	Approved
0.6019	Remote Similarity	NPD4634	Approved
0.6019	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD4138	Approved
0.6	Remote Similarity	NPD5364	Discontinued
0.6	Remote Similarity	NPD5205	Approved
0.6	Remote Similarity	NPD3617	Approved
0.6	Remote Similarity	NPD4688	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD4693	Phase 3
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD4690	Approved
0.6	Remote Similarity	NPD7521	Approved
0.6	Remote Similarity	NPD4689	Approved
0.6	Remote Similarity	NPD5690	Phase 2
0.598	Remote Similarity	NPD5128	Approved
0.598	Remote Similarity	NPD5168	Approved
0.5979	Remote Similarity	NPD4225	Approved
0.5978	Remote Similarity	NPD6051	Approved
0.5978	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5216	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